Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → trans-Ethyl 3-(4-cyano-3-fluorophenyl)-2-propenoate

HRID 412191Notes

Reaction equation

HRID 412191 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[F:11])#[N:2].[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:17]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][C:4]=1[F:11])#[N:2]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 112173392-Fluoro-4-formylbenzonitrile

Product 1

HCID 23021829trans-Ethyl 3-(4-cyano-3-fluorophenyl)-2-propenoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the product from Step A (970 mg, 6.5 mmol) and (carbethoxymethylene)triphenylphosphorane (2.3 g, 6.5 mmol) was heated at reflux in 50 mL of toluene overnight. The reaction was concentrated in vacuo, triturated with ether, and filtered. The filtrate was concentrated in vacuo, and purified by flash column chromatography on silica gel (15% EtOAc/hexane) to yield the desired product as a white solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customtriturated with ether
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by flash column chromatography on silica gel (15% EtOAc/hexane)

Sources & evidence

ORD record
ord-46d5cb59b29b42789a0de6b6994ab22f
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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