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Organic Lab Reactions 224

Organic Lab Reactions 224 - sis Isopropyl...

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REDUCTION OF KETONES 219 TABLE II— Continued REDUCTION OF KETONES WITH ALUMINUM ISOPROPOXIDE Compound Reduced 3-Acetoxystigmastadien- 5,22-one-7 Chlorogenone # Lupenalyl acetate Ethyl trimethylpyruvate Ethyl 2-methylcyclohex- anone-2-carboxylate Ethyl a-benzyliderie- acetoacetate Ethyl 0-benzoylpropi- onate Ethyl a-phenyl-0-ben- zoylpropionate Isopropyl benzophe- none-4-carboxylate Methyl 2-cis-phenyl-3- cts-benzoylcyclopro- pane-1-carboxylate Methyl 2-trans-phenyl- 3-cts-benzoylcyclopro- pane-1-carboxylate Methyl 2-trans-phenyl- 3-trans-benzoylcyclo- propane-1-carboxylate Methyl 2-cts-phenyl-3- trans-benzoylcyclopro- pane-l-carboxylate Product Formed Stereoisomers of stig- mastadien-5,22-diol-3,7 Mixture of chlorogenin and /3-chlorogenin Lupenediol (i) Keto Esters Isopropyl trimethyllac- tate Isopropyl 2-methylcyclo- hexanol-2-carboxylate {plus some ethyl ester) Ethyl a-benzylidene- 18-hydroxybutyrate (?) Y-Phenyl-7-butyrolactone a,7-Diphenyl-7-butyro-
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Unformatted text preview: sis) Isopropyl benzohydrol-4-carboxylate Lactone of 2-ct8-phenyl-3-cis-phenylhydroxy-methylcyclopropane-1-carboxylic acid (52%) (plus isopropyl ester of hydroxy acid) Lactone of hydroxy acid (19%) (plus isopropyl ester of hydroxy acid) Stereoisomeric mixture of isopropyl esters of hydroxy acid Stereoisomeric mixture of isopropyl esters of hy-droxy acid Reagent and Solvent * D D D D — C D D D U * u u u Yield 68% 78%^ (crude) 33% 66% 90% — 75% 95% 95% >52% >19% 82% — Refer-ence 153 154 73-36 155 5 74 156 36 40 40 40 40 Nora: 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 undistilled aluminum isopropoxide; D, to distilled reagent; and U, to an untreated solution of the alkoxide (see D. 199)....
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