Ethyl 2-(triphenylphosphoranylidene)propionate → Ethyl 2-methyl-3-(3,4,5-trifluorophenyl)acrylate

HRID 2185174Notes

Reaction equation

HRID 2185174 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[F:10])[CH:5]=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C=CC=CC=1>CN(C=O)C.C(OC(C)C)(C)C>[CH3:25][C:19](=[CH:5][C:4]1[CH:3]=[C:2]([F:1])[C:9]([F:10])=[C:8]([F:11])[CH:7]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 2

HCID 79792Ethyl 2-(triphenylphosphoranylidene)propionateHCID 27769543,4,5-Trifluorobenzaldehyde

Product 1

HCID 53919072Ethyl 2-methyl-3-(3,4,5-trifluorophenyl)acrylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7914Diisopropyl EtherSolvent

Procedure

1.0 eq. of 3,4,5-trifluorobenzaldehyde is dissolved in DMF and stirred at room temperature with 1.1 eq. of ethyl 2-(triphenylphosphanylidene)propionate until complete conversion can be determined by means of thin-layer chromatography. The mixture is freed from the solvent and the residue is stirred in diisopropyl ether. The insoluble residue is filtered off, the filtrate is concentrated in vacuo and the residue is chromatographed on silica gel (EA/heptane 1:1), the title compound being obtained in the form of a colorless solid. (M.p.: 66-68° C.).

Workup

  1. filtrationThe insoluble residue is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customthe residue is chromatographed on silica gel (EA/heptane 1:1)

Sources & evidence

ORD record
ord-d2f23468c05047f0b11850243ff787ae
Source dataset
uspto-grants-2002_06
Patent number
US06399824B1

Reaction notes

Loading…