Sodium borohydride → HCID 12656922, compound

Participants

Reaction Conditions

Reaction Steps

Following a procedure found in the literature (Ferguson, C. G.; Money, T.; Pontillo, J.; Whitelaw, P. D. M.; Wong, M. K. C. Tetrahedron. 52(47), 1996, 14661-14627) a solution of methyl 3-phenyl-3-methyl-2-oxobutanoate (2.5 g, 12 mmol, from Reference Example 36) in methanol (144 mL) is cooled to 0° C. (ice water bath). Sodium borohydride (0.21 g, 5.5 mmol) is added in three portions over 3 minutes. The reaction mixture is stirred at 0° C. for 10 minutes and then at room temperature for 30 minutes. The reaction mixture is quenched by the addition of 10% aqueous hydrochloric acid solution until pH=6 and then extracted thrice with diethyl ether. The combined extracts are washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfite, and concentrated under reduced pressure to give a light blond liquid, which is combined with the crude material from another reaction. The combined crude material is subjected to flash chromatography to (silica gel, hexanes/ethyl acetate) and provided 2.4 g (80% combined yield) of a clear, colorless oil. TOF MS (ES+): (M+H)=209.1

Provenance & Evidence