Organic Lab Reactions 222

Organic Lab Reactions 222 - diols Stereoisomeric estradiols...

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REDUCTION OF KETONES 217 TABLE II— Continued REDUCTION OF KETONBS WITH ALUMINUM ISOPBOPOXIDB Compound Reduced Benzoin Androsten-4-ol-17-one-3 3-Pinacol of androstene- 4-dione-3,17 16- (1 '-Methylpropyli- dene-) androsten-6-ol- 3-one-17 16-Benzylideneandro- sten-5-ol-3-one-17 Allopregnen-16-ol-3-one- 20 Pregnadien-5,16-oI-3- one-20 Ox-norcafestadienone 4-(2'-Hydroxy-l'-naph- thyl)-butanone-2 Equilenin Estrone Estrone benzyl ether Methoxyacetone a-Methoxyacetophenone 2-Methoxyacetophenone 3-Methoxyacetophenone 3,5-Dimethoxyvalero- phenone 2,5-Dimethoxypalmito- phenone Product Fonned Mesohydrobenzoin Stereoisomers of andro- stene-4-diol-3,17 3-Pinacol of androsten-4- ol-17-one-3 16-(1'-Methylpropyli- dene-) androstene-5- diol-3,17 (isolated as diacetate) 16-Benzylideneandro- stene-5-diol-3,17 Allopregnene-16-diol-3,- 20 Pregnadiene-5,16-diol-3,- 20 Ox-norcafestadienol (iso- lated as acetate) 4-(2'-Hydroxy-l '-naph- thyl)-butanol-2 Stereoisomeric equilenin
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Unformatted text preview: diols Stereoisomeric estradiols 3-Benzyl ether of .estra-diol l-Methoxypropanol-2 a-(Methoxymethyl-) benzyl alcohol a-Methyl-2-methoxy-benzyl alcohol a-Methyl-3-methoxy-benzyl alcohol a-Methyl-4-methoxy-benzyl alcohol n-Butyl-3,5-dimethoxy-phenyhnethanol Pentadecyl-2,5-dimeth-oxyphenylmethanol Reagent and Solvent * C D D D D D D D D U,D D D D D D D D Yield 90% 95% 81% 38% (crude) 52% (crude) 40% 43% 69% 92-100% "Good" 40% 72% 82% 80% 52% 66% Refer-ence 5 127,137 20 138 138 139 139 140 141 41, 142 143 144 17 17 36 36 36 36 145 Nora: References 81-158 appear on pp. 221-223 * Unleas otherwise stated, the reduction was carried out with aluminum isopropoxide in boiling iso-propyl alcohol solution. C refers to clarified but undisUlled aluminum isopropoxide; D, to distilled reagent; and U, to an untreated solution of the alkoiide (see p. 199),...
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