Water → 1-Benzyl-3-(5-Hydroxy-1,3-Decadien-1-yl)-Indole

HRID 845510노트

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HRID 845510 반응식
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=[O:22])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([Mg]Br)[CH2:24][CH2:25][CH2:26][CH3:27].O.C(OCC)(=O)C>O1CCCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[CH:18][CH:19]=[CH:20][CH:21]([OH:22])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 541315495-(1-Benzylindol-3-yl)-2,4-pentadienalHCID 178445865HCID 178445865, 화합물

생성물 1

HCID 539667671-Benzyl-3-(5-Hydroxy-1,3-Decadien-1-yl)-Indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 5-(1-benzylindol-3-yl)-2,4-pentadienal (2 g, 7 mmol) in 25 ml of tetrahydrofuran, stirred in a dry ice-acetone bath, was added in one portion 7 mmol of n-pentyl magnesium bromide (3.9 ml of 1.8M solution in ether). The resulting mixture was stirred at -78° C. for 90 min. and then mixed with 50 ml of water after warming up to about 0° C. Ethyl acetate, 50 ml, was added and the layers were separated. The organic layer was washed with water, dried (MgSO4) and concentrated on rotary evaporator to give the crude mixture. This substance was purified on a silica gel dry column (25% ethyl acetate in hexane) to afford 0.4 g of the produce as an oil. NMR spectrum shows a singlet at 5.12 and a multiplet centered at 4.05 ppm.

후처리

  1. temperatureafter warming up to about 0° C
  2. customthe layers were separated
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated on rotary evaporator

출처 및 근거

ORD 기록
ord-3641a9f214a3452881afadbb700cc1b3
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04758586

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