Ethyl 4-bromocinnamate → 2-Propen-1-ol, 3-(4-bromophenyl)-, (2E)-

HRID 1590378노트

반응식

HRID 1590378 반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8](OCC)=[O:9])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][CH2:8][OH:9])=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 141107Ethyl 4-bromocinnamateHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 533963712-Propen-1-ol, 3-(4-bromophenyl)-, (2E)-수율 87.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ethyl 4 -bromocinnamate (12.12 g) was dissolved in dry dichloromethane (50 ml) under nitrogen and cooled to -20°. Diisobutylaluminium hydride (100 ml, 1M solution in dichloromethane) (ex Aldrich) was added dropwise. The solution was allowed to warm to 25° then stirred for 18 hours then partitioned between ether and dilute hydrochloric acid. The organic phase was washed with saturated sodium bicarbonate, brine, dried over magnesium sulphate and concentrated under vacuum to give 3-(4-bromophenyl)prop-2-en-1-ol (8.9 g). NMR 1H: 7.28(2H,d), 7.05 (2H,d), 6.45 (1H,d), 6.25 (1H,t), 4.25 (2H,d), 2.0 (1H,s).

후처리

  1. temperaturecooled to -20°
  2. temperatureto warm to 25°
  3. customthen partitioned between ether and dilute hydrochloric acid
  4. washThe organic phase was washed with saturated sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-7d9b2d90cf8a469596d12bcca3003d5f
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05202356

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