Organic Lab Reactions 219

Organic Lab Reactions 219 - threne Androstadien-3,5-ol-17...

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214 REDUCTION WITH ALUMINUM ALKOXIDES -TABLE II— Continued REDUCTION OF KETONES WITH ALUMINUM ISOPKOPOXIDE Compound Reduced Axerophthylideneacetone Dihydrorhodoxanthin Capsanthin Benzalacetone Dibenzalacetone Dibenzalcyclopenta- "1 none Dibenzalcyclohexa- none Dicinnamalacetone Cinnamalacetophenone J Benzaldesoxybenzoin A 8 -l-Keto-5,10-dimethyl- 3-isopropenyloctahy- dronaphthalene (ere- mophHone) 3-Keto-l,2,3,9,10,10o- hexahydro-1,2-cyclo- pentanophenanthrene Androstadien-3,5-one-l 7 Cholesten-4-one-3 Cholesten-8-one-7 Cholestadien-4,7-one-3 Ergosten-8(14)-one-3 Product Formed Axerophthylideneiso- propyl alcohol Zeaxanthin Capsanthol Methylstyrylmethanol Distyrylmethanol Difficult to isolate the pure reduced com- pounds 1,2,3-Triphenylallyl alcohol A 8 -l-Hydroxy-5,10-di- methyl-3-isopropenyloc- tahydronaphthalene (eremophilol) 3-Hydroxy-l,2,3,9,10,- 10o-hexahydro-l,2-cy-
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Unformatted text preview: threne Androstadien-3,5-ol-17 Cholesten-4-ol-3 and epi-cholesten-4-ol-3 Chole8ten-8-ol-7 Cholestadien-4,7-ol-3 (35%) ep£-Cholestadien-4,7-ol-3 (49%) Cholestadien-5,7-ol-3 (15%) ejw-Cholestadien-5,7-ol-3 (1%) (estimated ratios) Ergosten-8(14)-ol-3 Reagent and Solvent * D D D D C, D C D D D D D D D • Yield 12% 23% 35% 58% 91% 75% (crude) 80% (crude) 35% 52% 44% — — Refer-ence 119,120 121 122 36 36 (5) • 5 123,124 125 126 127 35 128 34 129 NOTB: References 81-158 appear on pp. 221-223. * Unless otherwise stated, the reduction was carried out with aluminum isopropoxide in boiling iso-propyl alcohol solution. C refers to clarified but undistiUed aluminum isopropoxide; D, to distilled reagent; and U, to an untreated solution of the alkoxide (see p. 190)....
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