反応 #1605823

反応方程式

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

収率 42.5%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度the mixture was warmed gradually to 0° C
2. 2
   ろ過insoluble matter was filtered off
3. 3
   洗浄washed with tetrahydrofuran
4. 4
   workup.ADDITIONThe filtrate and the washing were mixed
5. 5
   濃縮concentrated under reduced pressure
6. 6
   workup.ADDITIONTo the residue was added
7. 7
   その他purified water (100 mL)
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature overnight
9. 9
   ろ過The precipitate was collected by filtration
10. 10
    洗浄washed with purified water
11. 11
    洗浄The precipitate was further suspension-washed with ethyl acetate (200 mL)
12. 12
    ろ過collected by filtration
13. 13
    その他dried under reduced pressure

実験手順

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).

出典