3-Thiophenecarboxaldehyde → 3-Thiophen-3-yl-acrylic acid ethyl ester

HRID 2371034Notes

Reaction equation

HRID 2371034 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.C1(P(=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[CH:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:2]1

Participants

4

Reactant 2

HCID 681353-ThiophenecarboxaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 669147533-Thiophen-3-yl-acrylic acid ethyl esterYield 83.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of thiophene-3-carbaldehyde (10 g, 89.3 mmol) in THF (500 mL) at 0° C. was added ethyl (triphenylphosphoranylidene)acetate (35 g, 100.5 mmol) in portions. After stirring overnight, the reaction mixture was concentrated and purified by column chromatography to give the title compound (13.6 g, 83%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-4a99e82d39a8437bb5058c770520a595
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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