2-(3-Chlorophenyl)-2-methylpropanal → 3-(3-Chlorophenyl)-3-methylbutan-2-ol

HRID 83867ノート

反応式

HRID 83867 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:13][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH3:11])[CH:9]([OH:10])[CH3:13])[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 820751242-(3-Chlorophenyl)-2-methylpropanalHCID 178418689HCID 178418689、化合物

生成物 1

HCID 667407143-(3-Chlorophenyl)-3-methylbutan-2-ol収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 2-(3-chlorophenyl)-2-methylpropanal (4.6 g, 25.7 mmol) in THF (150 mL) at 0° C. was added MeMgBr (3M in ether, 17.1 mL, 51.3 mmol, 2 eq) dropwise over 2 h. After stirring 1 h at 0° C., the reaction was allowed to warm to room temperature, quenched with 1N HCl and then extracted with EtOAc. The extracts were dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography (silica, Hex/EtOAc=20:1 to 10:1) to give 3-(3-chlorophenyl)-3-methylbutan-2-ol (3.9 g, 78%). 1H NMR (400 MHz, CDCl3) δ 7.36 (s, 1H), 7.28 (m, 2H), 7.18 (m, 1H), 3.85 (q, 1H), 1.32 (d, J=6.4 Hz, 6H), 1.05 (d, J=6.8 Hz, 3H).

後処理

  1. temperatureto warm to room temperature
  2. customquenched with 1N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe extracts were dried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography (silica, Hex/EtOAc=20:1 to 10:1)

出典と根拠

ORDレコード
ord-1fac463ae16c490bb91b476bfa4fc554
出典データセット
uspto-grants-2014_09
特許番号
US08846739B2

反応ノート

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