Dichloromethane → 2-Acetoxy-4-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrile

関与物質

反応手順

A mixture of 3-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]propionaldehyde (1.47 g), sodium cyanide (0.25 g), acetic anhydride (0.52 g), benzyltributylammonium chloride [(C4H9)3 (C6H5CH2)N+Cl- ](0.66 g) and dichloromethane (30 ml)- water (10 ml) was stirred at room temperature for 18 hours. The organic layer was separated, washed with water, dried (MgSO4) and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:2), 2-acetoxy-4-[4-[3-(5-methyl- 2-phenyl-4-oxazolyl)propionyl]phenyl]butyronitrile (1.75 g, quantitative) was obtained as an oily substance. NMR (δ ppm in CDCl3): 2.13 (3H, s), 2.15-2.3 (2H, m), 2.38 (3H, s), 2.8-3.0 (4H, m), 3.39 (2H, t, J=7 Hz), 5.29 (1H, t, J=6.5 Hz), 7.28 (2H, d, J=8 Hz), 7.35-7.5 (3H, m), 7.9-8.05 (4H, m)

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