反应详情

To a stirred ice-cooled solution of 291 mg of trans-6-Amino-3-chloro-α-cyclopropylethenyl-α-(trifluoromethyl)benzyl alcohol (from Example 5, Part C) in 13 mL of dry ether was added 0.180 mL of dry pyridine and 0.120 mL of bromopropionyl bromide. After 1 h, the reaction mixture was diluted with ether, washed with water and aqueous sodium bicarbonate, dried and evaporated. The residue was dissolved in 10 mL of dry DMF and was treated at 0° with 40 mg of 100% sodium hydride. After 15 min the cooling bath was removed and stirring was continued at ambient temperature for 20 h. The reaction was poured onto aqueous ammonium chloride and extracted with ether. The ether layer was washed with brine, dried and evaporated. The residue was dissolved in a small amount of ethyl acetate, and addition of hexane resulted in the crystallization of 40 mg of the title compound as colorless crystals: mp 171-172°; HRMS: Calcd. for C16H16NO2ClF3 (M+H)+: 346.082166. Found: 346.080681. A second crop of slightly less pure product weighed 41 mg.

1. washwashed with water and aqueous sodium bicarbonate
2. customdried
3. customevaporated
4. dissolutionThe residue was dissolved in 10 mL of dry DMF
5. additionwas treated at 0° with 40 mg of 100% sodium hydride
6. customAfter 15 min the cooling bath was removed
7. waitwas continued at ambient temperature for 20 h
8. additionThe reaction was poured onto aqueous ammonium chloride
9. extractionextracted with ether
10. washThe ether layer was washed with brine
11. customdried
12. customevaporated
13. dissolutionThe residue was dissolved in a small amount of ethyl acetate, and addition of hexane