2-Bromo-4-methylpyridine → (2-Fluoro-4-methylphenyl)(4-methyl-pyridin-2-yl)methanol

HRID 593383ノート

反応式

HRID 593383 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.C([Li])CCC.[F:14][C:15]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:16]=1[CH:17]=[O:18]>C(OCC)C>[F:14][C:15]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:16]=1[CH:17]([C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1)[OH:18]

参加物

5

反応物 3

HCID 27340872-Bromo-4-methylpyridineHCID 27784712-Fluoro-4-methylbenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 86703873(2-Fluoro-4-methylphenyl)(4-methyl-pyridin-2-yl)methanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 2-bromo-4-methylpyridine (600 mg) in diethyl ether (20 mL) at −78° C. is added a 2.3M solution of butyllithium in hexanes (1.52 mL). After stirring at this temperature for 1 hour 2-fluoro-4-methylbenzaldehyde is added and the mixture allowed to warm at room temperature. The reaction mixture is then hydrolyzed with diluted aqueous hydrochloric acid, washed with diethyl ether, basified with concentrated sodium hydroxide and extracted with diethyl ether. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (heptane/ethyl acetate 2/1) to afford (2-fluoro-4-methylphenyl)(4-methyl-pyridin-2-yl)methanol as a pale yellow oil which solidifies on standing.

後処理

  1. additionis added
  2. washhydrolyzed with diluted aqueous hydrochloric acid, washed with diethyl ether
  3. extractionextracted with diethyl ether
  4. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by chromatography over silica gel (heptane/ethyl acetate 2/1)

出典と根拠

ORDレコード
ord-074df675293540b282da776a35ed39e4
出典データセット
uspto-grants-2016_01
特許番号
US09242959B2

反応ノート

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