Tetrahydrofuran → 2-Ethenyl-1H-indole

HRID 2365872Notes

Reaction equation

HRID 2365872 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH:12]=O.[CH2:14]1COCC1>>[CH:12]([C:4]1[NH:3][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH2:14]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 96389Indole-2-carboxaldehyde

Product 1

HCID 109971472-Ethenyl-1H-indoleYield 83%

Procedure

NaH (2.6 g, 66.2 mmol) at 0° C. was added to a mixture of 1H-indole-2-carbaldehyde (4.00 g, 27.6 mmol) and PPh3CH3Br (19.7 g, 55.2 mmol) in dry THF (100 mL). After being stirred at room temperature for 16 hours, the reaction was quenched with water. After partition, the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine, dried, and concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (50:1) to give 2-vinyl-1H-indole (4.0 g, 83% yield) as a solid.

Workup

  1. customthe reaction was quenched with water
  2. customAfter partition
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with petroleum ether/ethyl acetate (50:1)

Sources & evidence

ORD record
ord-66658f4e821b474b85cb8865af4489cb
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

Loading…