Diisobutylaluminum hydride → 5-Bromo-2-(2-thienylmethoxy)benzenemethanol

HRID 1455967ノート

反応式

HRID 1455967 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([CH:11]=1)[C:7](OC)=[O:8].CC(C[AlH]CC(C)C)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[C:6]([CH:11]=1)[CH2:7][OH:8]

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 22105630Methyl 5-bromo-2-(2-thienylmethoxy)benzoate

生成物 1

HCID 289814405-Bromo-2-(2-thienylmethoxy)benzenemethanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-50 °C

実験手順

A solution of methyl 5-bromo-2-(2-thienylmethoxy)benzoate (1.6 g, 4.9 mmol) in dichloromethane (20 ml) was cooled to -85° C. A solution of DIBAL (5.8 ml, 1N in CH2Cl2) was added dropwise. The temperature was maintained below -75° C. for 30 minutes and then warmed to -50° C. over 21/2% hours. The reaction mixture was quenched with 1N HCl, washed with aqueous sodium hydrogen carbonate solution, dried (MgSO4) and evaporated. The product was purified by chromatography (eluant: diethyl ether/hexane) to give 5-bromo-2-(2-thienylmethoxy)benzyl alcohol a colourless gum (0.53 g, 36.4%).

後処理

  1. temperatureThe temperature was maintained below -75° C. for 30 minutes
  2. customThe reaction mixture was quenched with 1N HCl
  3. washwashed with aqueous sodium hydrogen carbonate solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe product was purified by chromatography (eluant: diethyl ether/hexane)

出典と根拠

ORDレコード
ord-e53d125e41db434381ce0c3b6a668494
出典データセット
uspto-grants-1998_12
特許番号
US05843942

反応ノート

読み込み中…