Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 3-(5-methylthiophen-2-yl)prop-2-enoate

HRID 651634Notes

Reaction equation

HRID 651634 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12]>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:12])[CH:13]=[CH:7][C:5]1[S:6][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 616635-Methyl-2-thiophenecarboxaldehyde

Product 1

HCID 53641428Methyl 3-(5-methylthiophen-2-yl)prop-2-enoateYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-methyl-thiophene-2-carboxaldehyde (5 g, 40 mmol) in CH2Cl2 (100 mL) is added methyl (triphenylphosphoranylidene) acetate (13.3 g, 40 mmol). The solution is stirred for 72 hours. After this time, the solution is concentrated. The residue is slurried in Et2O. The solution is filtered through a bed of Celite. The collected liquid is concentrated. The residue is purified by column chromatography eluting with a gradient of 50% EtOAc/hexanes to 60% EtOAc/hexanes to give the title compound (4.5 g, 25 mmol) as an oil.

Workup

  1. concentrationAfter this time, the solution is concentrated
  2. filtrationThe solution is filtered through a bed of Celite
  3. concentrationThe collected liquid is concentrated
  4. customThe residue is purified by column chromatography
  5. washeluting with a gradient of 50% EtOAc/hexanes to 60% EtOAc/hexanes

Sources & evidence

ORD record
ord-997cf3b78b544914ba3c89f3e3fa0ad6
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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