Organic Lab Reactions 221

Organic Lab Reactions 221 - Dimethylacetal of...

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216 REDUCTION WITH ALUMINUM ALKOXIDES TABLE II— Continued - REDUCTION OP KETONES WITH ALUMINUM ISOPROPOXIDE Compound Reduced Product Formed - Reagent and Solvent * Yield Refer- ence (/) Diketones Benzil 1,4-Dibenzoylbutane 1,8-Dibenzoyloctane 1,16-Dibenzoylhexa- decane Quinone 2-Methyl-2-phytyl-2,3- dihydro-l,4-naphtho- quinone Androsten-4-dione-3,17 Mesohydrobenzoin 1,6-Diphenylhexane- diol-2j5 1,1 O-Diphenyldecane- diol-2,9 1,18-Diphenylocta- decane-diol-2,17 Hydroquinone 2-Methyl-2-phytyl-l,2,- 3,4-tetrahydro-l,4- naphthohydroquinone cis- and trans-Androsten- 4-ol-17-one-3 C c u Al(O-t-C4H 9 ) 3 in «-C 4 H9OH 90% 100% 94% 70% 5 134 134 134 5 135 21 (g) Protected Diketones Dimethylacetal of phenylglyoxal 3-Enol ethyl ether of 16- benzalandrosten-4- dione-3,17 21-Dimethylacetal of pregnen-5-ol-3-one- 20-»l-21
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Unformatted text preview: Dimethylacetal of phenylglycollic alde-hyde 16-Benzalandrosten-4-ol-17-one-3 (isolated as. acetate) 21-Dimethylacetal of pregnen-5-diol-3,20-al-21 (isolated as diace-tate) D D D 55% 33% 68% 17 19 18 (ft) Alcoholic and Phenolic Ketones (and Ethers or Esters of These) Docosadien-1,21-ol-l 1-one-12 Docosadiene-l,21-diol-11,12 (a-isomer 22%, /3-isomer 60%) D 82% 136 NOTE: References 81-158 appear on pp. 221-223. * Unless otherwise stated, the reduction waB carried out with aluminum isopropoJride in boiling iso-propyl alcohol solution. C refers to clarified but undistilled aluminum isopropoxide; D, to distilled reagent; and V, to an untreated solution of the alkoxide (see p. 199). x...
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