Реакция #159755

Уравнение реакции

1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

NaBH4

→

6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine

Выход 91.0%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ДругоеExcess of NaBH4 was quenched
2. 2
   workup.ADDITIONby adding aq. NH4Cl, and ethanol
3. 3
   Другоеwas evaporated
4. 4
   ДругоеThe residue was partitioned between ethyl acetate and water
5. 5
   Другоеthe organic layer was separated
6. 6
   Промывкаwashed with brine (40 mL)
7. 7
   Сушкаdried over sodium sulphate
8. 8
   ДругоеCrude product obtained
9. 9
   Другоеafter evaporation of solvent
10. 10
    Другоеwas purified by silica gel column chromatography

Методика

To a stirred solution of 1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (8.6 g, 19.8 mmol) in ethanol (40 mL) was added NaBH4 (1.5 g, 39.0 mmol) portion wise and the reaction mixture was stirred overnight. Excess of NaBH4 was quenched by adding aq. NH4Cl, and ethanol was evaporated. The residue was partitioned between ethyl acetate and water, and the organic layer was separated, washed with brine (40 mL) and dried over sodium sulphate. Crude product obtained after evaporation of solvent was purified by silica gel column chromatography to furnish 6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (6.1 g).

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