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

HRID 351577Notes

Reaction equation

HRID 351577 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)=[CH2:2].[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].O>CN(C)C=O.C(OCC)(=O)C>[CH2:19]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH:1]=[CH2:2])[CH:8]=[CH:9]1)[CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-HCID 145674047-Ethenyl-1H-indole

Product 1

HCID 22556821Pent-4-en-1-yl-7-vinyl-1H-indoleYield 73.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22 °C

Procedure

To a 0° C. solution of 7-vinylindole (5.0 g, 34.9 mmol) in 140 mL of dimethylformamide was added sodium hydride (60% dispersion in mineral oil) (3.5 g, 87.3 mmol). The ice bath was removed and the solution was warmed to 20-24° C. and stirred an additional 30 minutes. 5-Bromo-1-pentene (20 mL, 175 mmol) was added dropwise and stirring continued for 3 hrs. The solution was poured into 150 mL of water and 150 mL of ethyl acetate. The aqueous layer was washed with additional ethyl acetate (3×100 mL) and the combined organic layers were washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 5-10% ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 5.39 g (73%) of the desired compound as a clear oil.

Workup

  1. customThe ice bath was removed
  2. stirringstirring
  3. waitcontinued for 3 hrs
  4. washThe aqueous layer was washed with additional ethyl acetate (3×100 mL)
  5. washthe combined organic layers were washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. washeluting with 5-10% ethyl acetate in hexanes
  10. additionFractions containing product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f70b4e9129f4d6ab18e3e3a0a8406ae
Source dataset
uspto-grants-2004_06
Patent number
US06743785B2

Reaction notes

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