Potassium Carbonate → HCID 66955572, compound

Participants

Reaction Conditions

Reaction Steps

4-Trifluoromethoxyphenol (0.375 mL, 2.89 mmol) was added to a mixture of epoxide 129 (250 mg, 1.15 mmol) and powdered K2CO3 (558 mg, 4.04 mmol) in anhydrous 2-butanone (3 mL) under N2, and the mixture was stirred at 81° C. for 12 h. The resulting cooled mixture was diluted with water (50 mL) and extracted with CH2Cl2 (4×50 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-25% EtOAc/petroleum ether firstly gave foreruns, and then further elution with 25-33% EtOAc/petroleum ether gave 4-(2-chloro-4-nitro-1H-imidazol-1-yl)-1-[4-(trifluoromethoxy)phenoxy]-2-butanol (130) (306 mg, 67%) as a pale yellow oil; 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.16 (br dd, J=9.1, 0.8 Hz, 2H), 6.88 (dt, J=9.2, 3.0 Hz, 2H), 4.37-4.24 (m, 2H), 4.02-3.93 (m, 2H), 3.86 (dd, J=10.0, 7.8 Hz, 1H), 2.47 (dd, J=4.2, 1.1 Hz, 1H), 2.13-1.98 (m, 2H); HRESIMS calcd for C14H14ClF3N3O3 m/z [M+H]+ 398.0540, 396.0569. found 398.0538, 396.0567.

Provenance & Evidence