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

HRID 845510Notes

Reaction equation

[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

Participants

Conditions

Temperature: -78 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-3641a9f214a3452881afadbb700cc1b3
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04758586

Reaction notes

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