Ethyl ketone → HCID 70138339, compound

Participants

Reaction Steps

Under a nitrogen atmosphere was combined 5 ml of acetic acid, 205 mg (0.62 mmol) of the title compound of Example 4 and 126 μl (1.25 mmol) of 3-pentanone, followed by 890 mg (6.29 mmol) of powdered sodium sulfate (Na2SO4). The solution was allowed to stir for 20 minutes, at which point 158 mg (0.75 mmol) of sodium triacetoxyborohydride (NaBH(OAc)3) was added. The solution was allowed to stir for 45 minutes and was then quenched with aqueous bicarbonate (75 ml) and was extracted with ethyl acetate (2×30 ml). The organic extract was washed with water (1×25 ml) and then brine (1×25 ml), and then dried over Na2SO4, filtered and concentrated in vacuo to afford 232 mg of crude product, which was chromatographed on silica gel using 9:1 hexane:ethyl acetate to afford 186 mg (74.7%) of the title compound.

Provenance & Evidence