Indole-7-carboxaldehyde → 7-Ethenyl-1H-indole

HRID 983937Notes

Reaction equation

HRID 983937 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH:7]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[CH:7]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)=[CH2:1]

Participants

6

Reactant 2

HCID 2734629Indole-7-carboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 145674047-Ethenyl-1H-indole

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl triphenylphosphonium bromide (5.05 g, 14.1 mmol) in tetrahydrofuran (80 mL) was added potassium tert-butoxide (1 M in tetrahydrofuran, 14.1 mL, 14.1 mmol) and the reaction stirred for 45 minutes at room temperature. Next a prepared solution of 7-formylindole (1.00 g, 6.89 mmol) in tetrahydrofuran (10 mL) was added and the reaction stirred for 1.5 hours. The reaction mixture was diluted with ethyl acetate (250 mL) and washed with an 8:1 mixture of water and 1 N hydrochloric acid (2×100 mL), saturated aqueous sodium chloride (100 mL), and dried over sodium sulfate. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide the desired compound as a brown oil.

Workup

  1. stirringthe reaction stirred for 1.5 hours
  2. washwashed with an 8:1 mixture of water and 1 N hydrochloric acid (2×100 mL), saturated aqueous sodium chloride (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a515d1225b84145a5ab94bc6fdfb025
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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