Diethyl Ether → 2-(5-Bromo-3-pyridyl)propan-2-ol

HRID 351739

반응식

HRID 351739 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:12]=1)C(OCC)=O.[CH3:13][Mg]Br.C([O:18][CH2:19][CH3:20])C>>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:19]([OH:18])([CH3:20])[CH3:13])[CH:12]=1

참가 물질

4

반응물 3

HCID 3283Diethyl Ether2회HCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

실험 절차

To a solution of ethyl 5-bromonicotinate (1.02 g, 4.4 mmol) in diethyl ether (15 mL) at −30° C. was added a 3M solution of methyl magnesium bromide in ether (4 mL, 12 mmol). The resulting slurry was refluxed for 2 hours then cooled and quenched with an excess of 0.5M aqueous monobasic sodium phosphate and partitioned between ether and water. The product from the organic phase was chromatographed on silica gel eluting with a 2:1:2 mixture of ether, pentane and ammonia-saturated methylene chloride to afford the 3-bromo-5-(1-hydroxy-1-methylethyl)pyridine compound as a yellow oil.

후처리

  1. temperatureThe resulting slurry was refluxed for 2 hours
  2. temperaturethen cooled
  3. customquenched with an excess of 0.5M aqueous monobasic sodium phosphate
  4. custompartitioned between ether and water
  5. customThe product from the organic phase was chromatographed on silica gel eluting with a 2:1:2 mixture of ether, pentane and ammonia-saturated methylene chloride

출처 및 근거

ORD 기록
ord-3f904e1c57c549b3b6f2c03ccbbd8aab
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743802B2

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