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

HRID 1455967노트

반응식

HRID 1455967 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-50 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e53d125e41db434381ce0c3b6a668494
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843942

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