A method for the synthesis of unsaturated carbonyl compounds

“…The formation of 9 was attributed to a deacylation of aldol product 2a, [26] which proceeded intramolecularly via 10 with the amine acting as base. This hypothesis was confirmed in a control experiment starting from 2a, which afforded 9 upon treatment with diethylamine (Scheme 4).…”

Section: Resultsmentioning

confidence: 99%

Iron(III)‐Catalyzed Tandem Sequential Methanol Oxidation/Aldol Coupling

Lecomte

Bolm

2005

Adv Synth Catal

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“…rx-Ethoxalyl-y-butyrolactone (6). Diethyl oxalate (11 g) was reacted wIth y-butyrolactone (5, 6.5g) as reported 13 ) to give 6 (lOg, 72% yield). MS m/z (%): 41 (41),55 (18), 69 (12), 86 (23),113 (100), and 186 (7) (3 and 4).…”

Section: Preparation Of (E)-(lnd (Z)-2-(4'-metlzyl-3'-pentellylidene)mentioning

confidence: 99%

(E)-2-(4′-Methyl-3′-pentenylidene)-4-butanolide, Namedβ-Acariolide: A New Monoterpene Lactone from the Mold Mite,Tyrophagus putrescentiae(Acarina: Acaridae)

Morino

Kuwahara

Matsuyama

et al. 1997

Bioscience, Biotechnology, and Biochemistry

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Reinwestigation of the opisthonotal gland secretion of the mold mite, Tyrophagus putrescentiae, resulted in the isolation of a new monoterpene lactone, whose chemical structure was elucidated as (E)-2-(4'-methyl-3'-pentenylidene)-4-butanolide (3), to which we gave the trivial name β-acariolide in relation to β-acaridial {1, (E)-2-(4-methyl-3-pentenylidene)-butanedial}. The compound was synthesized by LiAlH3 (OEt) reduction of 1 and subsequent oxidation involving simultaneous cyclization by using Ag2CO3 on Celite. Both the E- and Z-isomers of β-acariolide (3 and 4) were also prepared by the reaction of α-ethoxaly-γ-butyrolactone (6) and 4-methyl-3-pentenal under basic conditions. Their NMR spectra were compared with each other, and the geometry of the pentenylidene double bond of the isolated compound was concluded as being E.

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“…Usual work up gave 0.2 g of 3 (yield 54%). (8). To a stirred solution of 5 (2.2g, 20mmol) and 30% HzOz (7.2ml, 74mmol) in 70ml of methanol, was added 3N NaOH (3.2ml, 9.6mmol) dropwise at O°C, and then the mixture was stood in refrigerator for 22 hr.…”

Section: 3-dimethyl-5-morpholinomethyl-2-cyclopentenonementioning

confidence: 99%