반응 #1605823

반응 방정식

5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one

methanol

→

5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one

수율 42.5%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the mixture was warmed gradually to 0° C
2. 2
   여과insoluble matter was filtered off
3. 3
   세척washed with tetrahydrofuran
4. 4
   workup.ADDITIONThe filtrate and the washing were mixed
5. 5
   농축concentrated under reduced pressure
6. 6
   workup.ADDITIONTo the residue was added
7. 7
   기타purified water (100 mL)
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature overnight
9. 9
   여과The precipitate was collected by filtration
10. 10
    세척washed with purified water
11. 11
    세척The precipitate was further suspension-washed with ethyl acetate (200 mL)
12. 12
    여과collected by filtration
13. 13
    기타dried under reduced pressure

실험 절차

Under an argon flow, 5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (7.15 g, 17.8 mmol) was suspended in dehydrated tetrahydrofuran (40 mL), the CBS catalyst (493 mg) was added thereto, and the reaction mixture was stirred at −20° C. for 40 minutes. After adding dropwise a 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (21.4 mL) at the same temperature, the mixture was warmed gradually to 0° C. After adding methanol (20 mL) dropwise, insoluble matter was filtered off and washed with tetrahydrofuran. The filtrate and the washing were mixed and concentrated under reduced pressure. To the residue was added purified water (100 mL) and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration and washed with purified water. The precipitate was further suspension-washed with ethyl acetate (200 mL), collected by filtration, and dried under reduced pressure to obtain 5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (3.06 g).

출처