Ethyl 4-chloroacetoacetate → Ethyl 2-(2-(3-hydroxyphenyl)thiazol-4-yl)acetate

Participants

Reaction Steps

The procedure used for the preparation of 4a was repeated with 3-hydroxybenzenecarbothioamide 3d (1.53 g, 10.0 mmol ) and ethyl 4 -chloroacetoacetate (1.65 g, 10.0 mmol) in dry THF (20 mL) to give 4d (2.04 g, 78%) as a white solid after chromatographic purification on silica gel (gradient EtOAc/hexane: 30-40%) and recrystallization from EtOAc/hexane. mp 95.5°-97.2° C.; IR (KBr) 3112, 1727, 1278 cm-1 ; 1H NMR (DMSO-d6) δ1.15 (3H, t, J=7.0 Hz, CH3), 3.81 (2H, s, CH2), 4.07 (2H, g, J=7.0 Hz, CH2), 6.81 (1H, d, J=7.3 Hz, Ar), 7.22-7.30 (3H, m, Ar), 7.46 (1H, s), 9.68 (1H, s, OH); FDMS m/z 263 (M+); Anal. Calcd for C13H13NO3S: C, 59.30; H, 4.98; N, 5.32. Found: C, 59.41; H, 4.91; N, 5.30.

Provenance & Evidence