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Organic Lab Reactions 223

Organic Lab Reactions 223 -...

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218 REDUCTION WITH ALUMINUM ALKOXIDE8 TABLE il— Continued REDUCTION OP KETONBS WITH ALUMINUM ISOPBOPOXIDE Compound Reduced Benzoin methyl ether 4-Phenoxypropiophenone 4-(4'-Methoxyphenoxy-) propiophenone 3-Benzyloxy-4-methoxy- benzyl acetoxymethyl ketone 4-Propionyl-4'-methoxy- biphenyl l-Propionyl-4-methoxy- naphthalene 2-Propionyl-6-methoxy- naphthalene Estrone benzoate 3,17-Diacetoxyandro- sten-5-one-7 4,20-Diacetoxypregna- none-3 3-Acetate 16-(w-acetoxy- isocaproate) of allo- pregnanediol-3,16- one-20 3-Acetate 16-(«-acetoxy- isocaproate) of preg- nene-5-diol-3,16-one-20 3-Acetoxycholesten-5- one-7 3-ejn-Acetoxycholesten- 5-one-7 7-Ketocampesteryl ace- tate 3-Acetoxysitosten-5-one- 7 Product Formed Monomethyl ether of hydrobenzoin (stereo- isomers) Ethyl-4-phenoxyphenyl- methanol Etbyl-4- (4'-methoxyphe- noxy-)phenylmethanol 3-Benzyloxy-4-methoxy- benzylethylene glycol Ethyl-4'-methoxy-4-bi- phenylmethanol Ethyl-4-methoxy-l-naph- thylmethanol
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Unformatted text preview: Ethyl-6-methoxy-2-naph-thylmethanol 3-Benzoate of estradiols Androsten-5-triol-3,7,17 Pregnanetriol-3,4,20 AlIqpregnanetriol-3,16,20 Pregnene-5-triol-3,16,20 Stereoisomers of choles-ten-6-diol-3,7 Cholesten-5-diol-3-ept-7^a-(33%);7-^(25%) 7-Hydroxycampesterol (isolated as the diben-zoate) Stereoisomers of sitos-ten-5-diol-3,7 Reagent and Solvent • D D D D D D D C,D — D D D D — D Yield 83% — 90% 94% — — — 75% — — — — 63% 88% 40% 93% Refer-ence 17 86 86 42 86 86 86 5, 142 146 147 148 148 149,150 J30 151 152 NOTE- References 81-158 appear on pp 221-223 * TJnless otherwise stated.the reduction was carried out with aluminum isopropoxide in boiling ISO-propyl alcohol solution C refers to clarified but undistilled aluminum isopropoxide, D, to distilled reagent, and U, to an untreated solution of the alkoxide (see p 199)...
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