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

HRID 351739

反応式

HRID 351739 の反応式
[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

参加物

4

反応物 3

HCID 3283Diethyl Ether2 回HCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 178418573HCID 178418573、化合物

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3f904e1c57c549b3b6f2c03ccbbd8aab
出典データセット
uspto-grants-2004_06
特許番号
US06743802B2

関連ノート

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