Sodium borohydride → 2-Chloro-1-(6-fluorochroman-2-yl)ethanol

HRID 2423262노트

반응식

HRID 2423262 반응식
[Cl:1][CH2:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)=[O:4].[BH4-].[Na+]>C(O)C.O.ClCCl>[Cl:1][CH2:2][CH:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)[OH:4]

참가 물질

6

반응물 2

HCID 4311764Sodium borohydrideHCID 167553872-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone

생성물 1

HCID 672431242-Chloro-1-(6-fluorochroman-2-yl)ethanol수율 70%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A solution under stirring of 2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl)ethanone (0.33 g, 1.28 mmol, 88.4 A %) in ethanol (2.5 ml) was cooled to 0° C. under nitrogen. NaBH4 (60.1 mg, 1.59 mmol) was added to the solution and the reaction mixture stirred for 2 hours. After checking that the starting product had disappeared by GC, the mixture was diluted with demi water (7 ml) and dichloromethane (7 ml) and the phases separated. The organic stratum was dried under anhydrous sodium sulphate, filtered and concentrated under vacuum to give raw 2-chloro-1-(6-fluoro-3,4-dihydro-2H-chromen-2-yl) ethanol as a mixture of diastereoisomers 54:46 (0.30 g, 70% yield, 67.9 A %).

후처리

  1. customthe phases separated
  2. customThe organic stratum was dried under anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-63c947e7ab5145d2ab3af2f0f34bffe0
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960572B2

반응 노트

불러오는 중…