Acetaldehyde → HCID 68727908, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-phenoxyaniline (0.3 g, 1.62 mmol) in 1,2-dichloroethane (4 ml) were added N-(tert-butoxycarbonyl)-D-prolinal (0.322 g, 1.62 mmol) and sodium triacetoxyborohydride (0.480 g, 2.26 mmol). The resulting suspension was stirred overnight at 50° C. The mixture was then cooled to room temperature, water (8 ml) was added and extracted with ethyl acetate (3×20 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=70:30) to yield a light yellow oil that was dissolved in methanol (8 ml). Acetaldehyde (0.134 g, 3.05 mmol), zinc chloride (0.333 g, 2.44 mmol) and sodium cyanoborohydride (0.115 g, 1.83 mmol) were added and the mixture was stirred overnight at 40° C. Saturated ammonium acetate solution (10 ml) was added and extracted with ethyl acetate (3×30 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=70:30) to yield 0.43 g (67%) of a colourless oil; MS (ISP): 397.0 ((M+H)+.).

Provenance & Evidence