1-(Triphenylphosphoranylidene)acetone → Methyl 3-(3-oxo-1-butenyl)indole-6-carboxylate

HRID 278098Notes

Reaction equation

HRID 278098 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1)=O.[C:16]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:18])[CH3:17]>O1CCOCC1>[O:18]=[C:16]([CH3:19])[CH:17]=[CH:1][C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[NH:5][CH:4]=1

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 735867methyl 3-formyl-1H-indole-6-carboxylate

Product 1

HCID 53858282Methyl 3-(3-oxo-1-butenyl)indole-6-carboxylateYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 3-formylindole-6-carboxylate (368 mg) in 1,4-dioxane (10 ml) was added acetylmethylene triphenylphosphorane (1.15 g), and the mixture was stirred under reflux for 12 hours. The resulting mixture was evaporated in vacuo, redissolved with ethyl acetate and washed with 1N hydrochloric acid and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of chloroform and ethyl acetate (1:2) to give methyl 3-(3-oxo-1-butenyl)indole-6-carboxylate (75 mg) as a solid.

Workup

  1. temperatureunder reflux for 12 hours
  2. customThe resulting mixture was evaporated in vacuo
  3. dissolutionredissolved with ethyl acetate
  4. washwashed with 1N hydrochloric acid and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with a mixture of chloroform and ethyl acetate (1:2)

Sources & evidence

ORD record
ord-e5b7b3b9a0b94d1a9039241ad2e1a667
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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