반응 #797066

반응 방정식

NaHCO3

(R)-4-(6-Methoxy-quinazolin-2-yl)-4-methyl-oxazolidin-2-one

methylene chloride

boron tribromide

chloride

→

(R)-4-(6-Hydroxyquinazolin-2-yl)-4-methyloxazolidin-2-one

반응 조건

후처리

1. 1
   온도The reaction mixture was then warmed up to at 23° C. gradually
2. 2
   온도heated at 50° C. for 2 hours
3. 3
   기타DCM was removed under vacuum
4. 4
   기타the white solid was collected
5. 5
   세척washed with water and hexanes (560 mg, 69%)

실험 절차

(R)-4-(6-Methoxy-quinazolin-2-yl)-4-methyl-oxazolidin-2-one (860.0 mg, 3.317 mmol) was dissolved in methylene chloride (60 mL, 900 mmol), and cooled to −78° C. A solution of 1.0 M of boron tribromide in nethylene chloride (9.95 mL, 9.95 mmol) was then added dropwise. The reaction mixture was then warmed up to at 23° C. gradually and then heated at 50° C. for 2 hours. The reaction mixture was then question with NaHCO3 (sat) to basic, and neutralized back to pH-7-8. DCM was removed under vacuum, the white solid was collected and washed with water and hexanes (560 mg, 69%). 1H NMR (MeOD) δ: 9.32 (s, 1H), 7.91 (d, J=9.3 Hz, 1H), 7.57 (dd, J=9.0, 2.8 Hz, 1H), 7.26 (d, J=2.5 Hz, 1H), 4.98 (d, J=8.5 Hz, 1H), 4.46 (d, J=8.5 Hz, 1H), 1.78 (s, 3H). MS (M+1): 246.10.

출처