Pyridine → 3-Nitro-1-(4-octylphenyl)propyl acetate

Participants

Reaction Steps

To a solution of 3-nitro-1-(4-octylphenyl)propan-1-one (12) (5.00 g) in methanol (25 ml) was added sodium borohydride (0.8 g) at 0° C. and the mixture was left at room temperature for 4.5 hr. The suspension was diluted with ethyl acetate and washed successively with 1 N HCl, sodium bicarbonate solution and brine. The ethyl acetate layer was dried over anhydrous Na2SO4 and concentrated. To the residue was added pyridine (1.5 eq), dichloromethane (10 v) and acetic anhydride (10 eq), and the mixture was left at room temperature overnight. To the reaction mixture was added ice water and the mixture was extracted with ethyl acetate and washed successively with 1 N HCl, sodium bicarbonate solution and brine. The ethyl acetate solution was dried over sodium sulfate and concentrated. The residue was pure enough for transformation to the next step or can be purified by silica gel column chromatography using hexane-ethyl acetate as eluent. Yield=94%, ESIMS 358.2 [M+Na]+

Provenance & Evidence