Diisobutylaluminumhydride → 4-Phenyl-but-3-enylamine

HRID 6714노트

반응식

HRID 6714 반응식
[C:1]1([CH:7]=[CH:8][CH2:9][C:10]([NH2:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[C:1]1([CH:7]=[CH:8][CH2:9][CH2:10][NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 21225700DiisobutylaluminumhydrideHCID 540149774-Phenyl-but-3-enoic acid amide

생성물 1

HCID 537132274-Phenyl-but-3-enylamine수율 79.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A suspension of 4-phenyl-but-3-enoic acid amide (5.0 g, 31 mmol) in 250 mL dichloromethane was cooled to 0° C. Diisobutylaluminum hydride (1 M in dichloromethane, 250 mL) was added and the resulting homogeneous mixture was allowed to slowly warm to rt. The reaction was stirred for 4 days then quenched by carefully pouring the mixture onto 200 mL of 1:1 water/methanol at 0° C. The aluminum salts were removed by filtration and washed with methanol. The combined filtrate was collected and the volatile material was removed by a rotary evaporator to give of 4-phenyl-but-3-enylamine (3.62 g, 79%) as a pale yellow oil.

후처리

  1. temperatureto slowly warm to rt
  2. customthen quenched
  3. additionby carefully pouring the mixture onto 200 mL of 1:1 water/methanol at 0° C
  4. customThe aluminum salts were removed by filtration
  5. washwashed with methanol
  6. customThe combined filtrate was collected
  7. customthe volatile material was removed by a rotary evaporator

출처 및 근거

ORD 기록
ord-66725a1049364b39b741a7bdee9695b0
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084154B2

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