A Convenient Method for Determining the Concentration of Grignard Reagents

Lin, Hung‐Yu; Paquette, Leo A.

doi:10.1080/00397919408010560

Cited by 103 publications

(97 citation statements)

References 8 publications

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“…10-Bromo-1-decanol was protected by using chloromethyl methyl ether to provide methoxymethyl ether 3. The cross coupling reaction between compound 3 and hexadecyl magnesium bromide catalyzed by Li 2CuCl4 yielded hexacosanol derivative 4 in a moderate yield (58%) (7,8). Cahiez et al reported the addition of N-methylpyrrolidone improved Cu-catalyzed cross coupling (9).…”

Section: Synthesis Of Hexacosanoic Acidmentioning

confidence: 99%

Chemical Synthesis of a Very Long-Chain Fatty Acid, Hexacosanoic Acid (C26:0), and the Ceramide Containing Hexacosanoic Acid

Yamamoto

Itoh

2015

J Nutr Sci Vitaminol

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Summary Hexacosanoic acid (C26:0) (1), a very long-chain fatty acid, is related to various diseases such as adrenoleukodystrophy (ALD), adrenomyeloneuropathy (AMN) and atherosclerosis. As the level of 1 higher than the normal is related to diseases above, hexacosanoic acid (1) and the ceramide 2, which contains 1, are thought to play an important role in various tissues. Hexacosanoic acid (1) is known to be a waxy solid and to be hard to dissolve in water as well as organic solvents. Due to this physical property, it is not easy to handle hexacosanoic acid (1) in a laboratory. Therefore, efficient chemical synthesis of the compounds 1 and 2 has not been reported. Here, we report a versatile synthetic method for hexacosanoic acid (1) and the ceramide 2 containing the fatty acid 1. Synthesis of hexacosanoic acid (1) was achieved by applying the coupling of two alkyl units as a key step. Ceramide 2 was efficiently synthesized by applying the reported procedure together with hexacosanoic acid (1) synthesized here. This synthetic strategy has an advantage of getting various carbon chain length fatty acids and their ceramides by using a variety of carbon chain units. This method is also applicable for large-scale synthesis. In addition, these compounds 1 and 2 are useful for investigation of details of these compounds related to diseases such as ALD and AMN.

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Section: Synthesis Of Hexacosanoic Acidmentioning

confidence: 99%

Chemical Synthesis of a Very Long-Chain Fatty Acid, Hexacosanoic Acid (C26:0), and the Ceramide Containing Hexacosanoic Acid

Yamamoto

Itoh

2015

J Nutr Sci Vitaminol

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“…Titration tests for the mixed electrolytes were conducted using methanol (organic synthesis grade; Kanto Chemical Co. Ltd.) diluted by five times the volume of tetrahydrofuran (THF; battery grade; Kanto Chemical Co. Ltd.) containing 0.2 g dm ¹3 of 1,10-phenenthroline (Kanto Chemical Co. Ltd.). 27 These operations were conducted in a glove box filled with argon. The magnesium deposition-dissolution was assessed using cyclic voltammetry.…”

Section: ¹3mentioning

confidence: 99%

Solution Structure and Magnesium Deposition Electrochemistry of Mixing Alkylmagnesium Halide with Magnesium Sulfonyl Amide/Glyme Solution

Egashira

Hiratsuka

2016

Electrochemistry

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To elucidate effective species and their quantitative requirements for reversible magnesium deposition, a triglyme solution of ethylmagnesium bromide (EtMgBr) complex was mixed with magnesium bis(trifluoromethanesulfonyl) amide/triglyme solution in various ratios. The mixed electrolyte characteristics have been assessed using electrochemical magnesium deposition tests, titration of methanol, and Raman spectroscopy. The existence of EtMgBr reduces the overpotential of magnesium deposition. The Coulombic efficiency of this process varies linearly with the EtMgBr content, although the active EtMgBr decreases more than expected from the mixing ratio. Raman spectra for the mixed electrolyte suggest a change in the structure of magnesium bromide species and coordination mode of magnesium by mixing of EtMgBr with magnesium sulfonylamide salt.

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“…Both TMPMgCl·LiCl and TMP 2 Zn·2 MgCl·2 LiCl have been employed for the metalation of imidazoles 9. Fully functionalized imidazoles 11 were obtained after quenching the resulting metalated imidazole derivatives 10 and 10' [10] with a broad range of electrophiles.…”

Section: Angewandte Communicationsmentioning

confidence: 99%

“…[3,5] Treatment of imidazoles 6 with iPrMgCl·LiCl [15] (1.2 equiv) at À78 8C led within 1 h to the corresponding Mg species 7 in quantitative yield. [10,16] Subsequently, various functionalization reactions were carried out to furnish the corresponding 4-and 5-substituted imidazoles 8 (Table 2).…”

Section: Angewandte Communicationsmentioning

confidence: 99%

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Full Functionalization of the Imidazole Scaffold by Selective Metalation and Sulfoxide/Magnesium Exchange

2013

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A simple, flexible, and straightforward method for the functionalization of all the positions of the imidazole heterocycle through regioselective arylations, allylations, acylations, and additions to aldehydes is disclosed. Starting from the readily available key imidazole 1, highly functionalized imidazole derivatives have been synthesized in a regioselective manner from directed metalations and a sulfoxide/magnesium exchange. Moreover, the selective N3-alkylation followed by deprotection of N1 (trans-N-alkylation) allows the regioselective N-alkylation of complex imidazoles.

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A Convenient Method for Determining the Concentration of Grignard Reagents

Cited by 103 publications

References 8 publications

Chemical Synthesis of a Very Long-Chain Fatty Acid, Hexacosanoic Acid (C26:0), and the Ceramide Containing Hexacosanoic Acid

Chemical Synthesis of a Very Long-Chain Fatty Acid, Hexacosanoic Acid (C26:0), and the Ceramide Containing Hexacosanoic Acid

Solution Structure and Magnesium Deposition Electrochemistry of Mixing Alkylmagnesium Halide with Magnesium Sulfonyl Amide/Glyme Solution

Full Functionalization of the Imidazole Scaffold by Selective Metalation and Sulfoxide/Magnesium Exchange

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