3-(1-(4-Fluorophenyl)cyclohexyl)propanoyl chloride → 2-(2-(1-(4-Fluorophenyl)cyclohexyl)ethyl)-7-vinyl-4,5-dihydronaphtho[1,2-d]oxazole

Participants

Reaction Steps

To a solution of 3-(1-(4-fluorophenyl)cyclohexyl)propanoyl chloride (Preparation 42B, 215 mg, 0.799 mmol) and 6-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime (Intermediate 1, 224 mg, 1.199 mmol) in 1,2-dichlorobenzene (2 mL) was added 4-(dimethylamino)pyridine (6.15 mg, 0.050 mmol), and the mixture was microwaved at 180° C. for 10 mins. The mixture of was purified by Combiflash (silica gel, 24 g) eluting with 5:95 followed by 2:8 ethyl acetate-hexane to give the desired 2-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)-7-vinyl-4,5-dihydronaphtho[1,2-d]oxazole (47 mg, 14.6% yield) as an oil. LC/MS M+1=402.26.

Provenance & Evidence