Diethyl Ether → 1-(2-Bromopyridin-4-yl)-propan-1-ol

HRID 1423044노트

반응식

HRID 1423044 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1.[CH2:10]([Mg]Cl)[CH3:11].CCOCC>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:9])[CH2:10][CH3:11])[CH:5]=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 27629912-Bromo-4-pyridinecarboxaldehydeHCID 178461633HCID 178461633, 화합물

생성물 1

HCID 866408041-(2-Bromopyridin-4-yl)-propan-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a chilled (−78° C.) solution of 2-bromopyridine-4-carboxaldehyde (7.0 g, 38 mmol) in THF (200 mL) is added a 2 M solution of ethylmagnesium chloride in ether (23.5 mL, 47.0 mmol) over a 10 minute period. After 15 minutes, the mixture is gradually warmed to room temperature over 1 hour. The reaction is quenched by the slow addition of saturated aqueous NH4Cl (100 mL) and extracted with EtOAc (2×200 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material is purified by silica gel chromatography eluting with a gradient of 20-40% EtOAc in hexanes to afford 1-(2-bromopyridin-4-yl)-propan-1-ol.

후처리

  1. customThe reaction is quenched by the slow addition of saturated aqueous NH4Cl (100 mL)
  2. extractionextracted with EtOAc (2×200 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material is purified by silica gel chromatography
  8. washeluting with a gradient of 20-40% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-be93e4dcde25446ea7882c48c797959d
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927550B2

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