Aldehydes Derived From Cortisone and Hydrocortisone

Rogers, E. F.; Leanza, W. J.; Conbere, J. P.; Pfister, K.

doi:10.1021/ja01131a525

Cited by 14 publications

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“…Nitrone formation and hydrolysis have also found a use in steroid chemistry (18,19,185). The 21-aldehydes of cortisone, hydrocortisone, and dihydrocortisone have been prepared from the corresponding 21-methyl compounds by employing the King reaction followed by nitrone formation and hydrolysis (159,181,192). The 21-aldehydes of 9-(a-fluoro)-or 9-(achloro) hydrocortisone were prepared similarly (86, 87), as were other 21-aldehydes (58,235) and 17glyoxals (171,184) in the pregnane series.…”

Section: Solvolysismentioning

confidence: 99%

Nitrones

Hamer¹,

Macaluso²

1964

Chem. Rev.

435

127

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Section: Solvolysismentioning

confidence: 99%

Nitrones

Hamer¹,

Macaluso²

1964

Chem. Rev.

435

127

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“…The analytical sample was obtained from the same solvent pair; m.p. 185-188°, [a]™D +179°, X"*xcli 5.80 (inflection) and 5.86 µ.…”

mentioning

confidence: 99%

Studies in Organic Sulfur Compounds. V.¹ Synthesis of 21-Thiolacetates of Adrenal Cortical Hormones

Djerassi¹,

Nussbaum²

1953

J. Am. Chem. Soc.

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This compound was then converted to 5-methoxy-2thenoic acid (III) by stirring overnight 3.60 g. of the halide with 0.90 g. of magnesium and 1 ml. of ethyl bromide.The cloudy mixture was then poured onto a slurry of Dry Ice and ether and the reaction products worked up as usual. There was obtained 0.60 g. (20%) of white needles, m.p. 161-162°( dec.), which did not depress the melting point of authentic III.No other material could be isolated from the mother liquors.Acylation of 2-Methoxythiophene. A. 5-Methoxy-2acetothienone.-A solution of 2.0 g. of I in 5 ml. of dry carbon disulfide, cooled to -20°, was added in 3 portions over a 10-minute period to a solution of acetyl chloride (1.2 ml.) and stannic chloride (2.0 ml.) in carbon disulfide (15 ml.) maintained at -20°, and then kept at that temperature for 5 additional minutes. The purple, heterogeneous mixture was then poured on ice (10 g.) and hydrochloric acid (1.0 ml.). The solvent layer was rapidly decanted, washed with water and saturated aqueous sodium bicarbonate.It was dried over sodium carbonate and evaporated, leaving a yellow oil (1.73 g.). The oil was chromatographed over 35.0 g. of alumina. Mixtures of hexane and benzene (9:1 and 4:1) eluted 0.76 g. of material which distilled at 60°( 0.001 mm.). The distillate (0.42 g.) crystallized in yellow needles which became colorless and melted at 34r-35°after recrystallization from hexane; X®'£H 2560 and 3140 Á. («, respectively, 4,100 and 14,200).

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IV. Synthesen über Nitrone

1953

Angewandte Chemie

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farblos, WaSSerloslich Versuoh: In einem Reagenzglas versetzt man etwa 20 mg 9-Fluorenyl-pyridiniumsalz in Wasser mit 2 n Kaliumoarbonat-Losung: keine erkennbare Veranderung (XVI A + XVIB; das C-Betain ist, da wasserunloslioh, nicht begdnstigt). Man gibt nun Chloroform hinzu, das sich bereits hellblau unten ansammelt und beim Schutteln tiefblau wird (XVI + XVII: im Chloroform ist das C-Betain begiinstigt). Einen Teil der blauen Chloroform-Losung pipettiert man ab und sohuttelt mit reiohlich Wasser: das Chloroform wird farblos (oder auoh sehwach gelb infolge beginnender Zersetzung des empfindliohen C-Betains) : XVII + XVI. Versetzt man nun das uberstehende Wasser mit 2 n Natronlauge und schiittelt erneut, so wird das Chloroform blau. F. Suchs u. R. Kernpf, ebenda 35, 1224 [1902]. Angew. Chem. / 65. Jahrg. 1953 Nr. 24 [1948] (Oxydation von Vitamin A zum Retinen. s. auch k. L . Wendler H . L. Slates u. M . Tishler J. Amer.'chem. SOC. 71 3267 [1969]. 72, 440 [1939]. lo) Fur Thiophen-2-glyoxal scheint auch die direkte Oxydation des 2-Acetyl-thiophens mit S e 0 8 gute Resultate zu geben: F . K i pnis I . Ornfelt J. Amer. chem. SOC. 68 27, 34 [1946]. 11) Heiv. Chim. Acta 24 904, 913/5 [i941j. 12) Gazz. chim. ital. 72,'363 [1942]; 78, 742/7 [1948].

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Aldehydes Derived From Cortisone and Hydrocortisone

Cited by 14 publications

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Nitrones

Nitrones

Studies in Organic Sulfur Compounds. V.¹ Synthesis of 21-Thiolacetates of Adrenal Cortical Hormones

IV. Synthesen über Nitrone

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Aldehydes Derived From Cortisone and Hydrocortisone

Cited by 14 publications

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Nitrones

Nitrones

Studies in Organic Sulfur Compounds. V.1 Synthesis of 21-Thiolacetates of Adrenal Cortical Hormones

IV. Synthesen über Nitrone

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Studies in Organic Sulfur Compounds. V.¹ Synthesis of 21-Thiolacetates of Adrenal Cortical Hormones