Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 13707691, compound

HRID 1160238Notes

Reaction equation

HRID 1160238 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C1(P(=[CH:31][C:32]([O:34][CH3:35])=[O:33])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6](/[CH:10]=[CH:31]/[C:32]([O:34][CH3:35])=[O:33])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 589040Indole-5-carboxaldehyde

Product 1

HCID 13707691HCID 13707691, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1H-indole-5-carbaldehyde (0.217 g, 1.5 mmol) and methyl (triphenylphosphoranylidene)acetate (0.535 g. 1.6 mmol) in DCM (4 mL) was stirred in a flask under reflux overnight, then the solvent was removed under reduced pressure. Purification by silica gel column chromatography, with a mixture of DCM/Hexane 8:2 as eluent system, gave 0.291 g of methyl (2E)-3-(1H-indol-5-yl)acrylate (97% yield).

Workup

  1. temperatureunder reflux overnight
  2. customthe solvent was removed under reduced pressure
  3. customPurification by silica gel column chromatography
  4. additionwith a mixture of DCM/Hexane 8:2 as eluent system

Sources & evidence

ORD record
ord-0e01b231ecff4a08b39a0b5ebc6f2013
Source dataset
uspto-grants-2010_10
Patent number
US07816386B2

Reaction notes

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