Water → Pent-4-en-1-yl-7-vinyl-1H-indole

HRID 557169Notes

Reaction equation

[H-].[Na+].[CH:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][CH:11]=[CH:10]2)=[CH2:4].Br[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].O>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[CH:6][C:5]=2[CH:3]=[CH2:4])[CH:10]=[CH:11]1)[CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

Conditions

Temperature: 22 °C

Procedure

Add sodium hydride (60% dispersion in mineral oil) (3.5 g, 87.3 mmol) to a 0° C. solution of 7-vinylindole (5.0 g, 34.9 mmol) in 140 mL of dimethylformamide. Warm the resulting mixture to 20-24° C. and stir an additional 30 minutes. Add 5-bromo-1-pentene (20 mL, 175 mmol) dropwise and stir for 3 hours. Pour the reaction mixture into a mixture of 150 mL of water and 150 mL of ethyl acetate. Wash the aqueous layer with ethyl acetate (3×100 mL). Combine the organic layers, wash with saturated aqueous sodium chloride, dry over sodium sulfate, filter, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 5-10% ethyl acetate in hexanes. Combine fractions containing product and concentrate them under reduced pressure to provide the desired compound as a clear oil (5.39 g, 73%).

Workup

additionPour the reaction mixture
washWash the aqueous layer with ethyl acetate (3×100 mL)
washCombine the organic layers, wash with saturated aqueous sodium chloride
dry with materialdry over sodium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
washeluting with 5-10% ethyl acetate in hexanes
additionCombine fractions containing product
concentrationconcentrate them under reduced pressure

Sources & evidence

ORD record: ord-3bc53e7e0f5b4bf7b406695281491d21
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058425B2

Reaction notes

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