Tetrahydrofuran → 2-Ethenyl-1H-indole

HRID 1774226Notes

Reaction equation

HRID 1774226 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-0bbcadc6858d44979e4967e3183376d3
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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