methyl (E,E)-5-(3beta,14beta-dihydroxy-5beta-androstane-17beta-yl)-2,4-pentadienoate → (E,E)-5-(3beta,14beta-dihydroxy-5beta-androstane-17beta-yl)-2,4-pentadien-1-ol

Participants

Reaction Steps

To a solution of 7.95 g of methyl (E,E)-5-(3β,14β-dihydroxy-5β-androstane-17β-yl)-2,4-pentadienoate (Boutagy J. and Thomas R., Aust. J. Pharm. Chem., 1972, NS1, 67) in 390 ml of dry tetrahydrofuran, 133 ml of 1M i-Bu2AlH in hexane were added dropwise under nitrogen at -78° C. After 2 hrs the reaction was quenched with aqueous sodium sulfate (63 g in 390 ml of water) and stirred at room temperature overnight. The mixture was then filtered through Celite and washed with ethyl acetate. The organic solution was dried over anhydrous sodium sulfate and evaporated to dryness to give 4.90 g of (E,E)-5-(3β,14β-dihydroxy-5β-androstane-17β-yl)-2,4-pentadien-1-ol as an off-white solid.

Provenance & Evidence