Potassium tert-butoxide → HCID 13767613, compound

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Reaction Steps

To a solution of 4.6 g of [3aS-[3a alpha, 3(R*,R*), 7beta, 7a beta]]-3-(3-Bromo-4-hydroxy-1-methylbutyl)hexahydro-3a-methyl-1H-inden-7-ol in 145 mL of dry t-butanol under an argon atmosphere and at room temperature is added 2.1 g of potassium t-butoxide. After stirring 50 minutes the mixture was cooled in an ice bath and 10 mL of saturated aqueous sodium dihydrogen phosphate was added. The mixture was stirred 10 minutes then poured into 500 mL of ice water and extracted 3×200 mL of methylene chloride. The combined extracts were washed successively with water, brine then dried over anhydrous sodium sulfate. Filtration and evaporation of solvent in vacuo gave 3.5 g of crude product. Medium pressure liquid chromatography eluting with hexane/ethyl acetate (1:1) gave 2.9 g (84%) of [3aS[3a alpha,3(R*,S*),7beta, 7a beta]]-Hexahydro-3a-methyl-3-(1-methyl-2-oxiranylethyl)- 1H-inden-7-ol. The analytical sample was crystallized from hexane/ethyl acetate. MP 62.5°-63° C.; [α]D25 -31.26° (c 1.0300, CHCl3). Calculated for C15H24O2 : C, 76.23; H, 10.24. Found: C 75.95; H, 10.01.

Provenance & Evidence