反应详情

温度

0 °C

6-Chloro-4-cyclopropyl-4-vinyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (590 mg, 2.36 mmol) was dissolved in dichloromethane (2.5 mL) and methanol (2.5 mL), and the resulting solution was stirred at −78° C. in an ozone atmospher. After it was confirmed by thin-layer chromatography that the raw materials disappeared, the ozone atmospher was replaced by a nitrogen atmospher, and the solution was stirred for 5 minutes. The temperature of the reaction solution was raised to 0° C., and sodium borohydride (26.8 mg, 7.1 mmol) was added thereto. The reaction solution was stirred at 0° C. for 30 minutes, and then, acetone was added thereto to stop the reaction. After the solvent was evaporated under reduced pressure, water (50 mL) and 1 N hydrochloric acid were added to the residue and the pH thereof was adjusted to about 4, and then, the solution was stirred at room temperature. The resulting white solid was collected by filtration, washed with water and then dried under reduced pressure, whereby the objective compound (487 mg, 81%) was obtained.

1. stirringThe reaction solution was stirred at 0° C. for 30 minutes
2. customthe reaction
3. customAfter the solvent was evaporated under reduced pressure, water (50 mL) and 1 N hydrochloric acid
4. additionwere added to the residue
5. stirringthe solution was stirred at room temperature
6. filtrationThe resulting white solid was collected by filtration
7. washwashed with water
8. dry with materialdried under reduced pressure, whereby the objective compound (487 mg, 81%)
9. customwas obtained