Sodium borohydride → 1-(5-Bromopyridin-2-yl)ethanol

HRID 1501109노트

반응식

HRID 1501109 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:10])[CH3:9])=[N:6][CH:7]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 231453451-(5-Bromopyridin-2-yl)ethan-1-one

생성물 1

HCID 426142881-(5-Bromopyridin-2-yl)ethanol수율 90%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 1-(5-bromopyridin-2-yl)ethanone (1.1 g, 5.5 mmol) in ethanol (100 mL) was added sodium borohydride (2.5 g, 66.1 mmol). The reaction mixture was stirred at room temperature for 24 hours. The mixture was filtered, the filtrate was acidified and the solvent removed on a rotary evaporator. The residue was taken up with water (50 mL) and extracted with dichloromethane (50 mL). The combined extract was dried over sodium sulfate, filtered, concentrated and purified by column chromatography to give 1-(5-bromopyridin-2-yl)ethanol (1.0 g, 90.0%) as a yellow oil. LRMS (M+H+) m/z: calcd 201.98. found 202. 1H NMR (300 MHz, CD3OD) δ 8.54 (d, J=2.4 Hz, 1H), 7.98 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 4.85 (m, 1H), 1.45 (d, J=6.6 Hz, 3H).

후처리

  1. filtrationThe mixture was filtered
  2. customthe solvent removed on a rotary evaporator
  3. extractionextracted with dichloromethane (50 mL)
  4. extractionThe combined extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-8b24fbd6904b4b5787ece5fd6c5195c1
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206128B2

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