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

HRID 845510ノート

反応式

HRID 845510 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3641a9f214a3452881afadbb700cc1b3
出典データセット
uspto-grants-1988_07
特許番号
US04758586

反応ノート

読み込み中…