Réaction #1605823

Équation de réaction

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

Rendement 42.5%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was warmed gradually to 0° C
2. 2
   Filtrationinsoluble matter was filtered off
3. 3
   Lavagewashed with tetrahydrofuran
4. 4
   workup.ADDITIONThe filtrate and the washing were mixed
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   workup.ADDITIONTo the residue was added
7. 7
   Autrepurified water (100 mL)
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature overnight
9. 9
   FiltrationThe precipitate was collected by filtration
10. 10
    Lavagewashed with purified water
11. 11
    LavageThe precipitate was further suspension-washed with ethyl acetate (200 mL)
12. 12
    Filtrationcollected by filtration
13. 13
    Autredried under reduced pressure

Mode opératoire

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).

Source