Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 88484438, compound

HRID 1590406Notes

Reaction equation

HRID 1590406 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:11][C@H:10]2/[CH:12]=[C:13](\[F:16])/[CH:14]=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:17]([CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH2:20][CH3:21])=[O:18]>ClCCl>[CH2:20]([O:19][C:17](=[O:18])/[CH:22]=[CH:14]/[C:13](/[F:16])=[CH:12]\[C@@H:10]1[CH2:11][C@H:9]1[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH3:21]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 18651183HCID 18651183, compound

Product 1

HCID 88484438HCID 88484438, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above aldehyde (0.5 g) was dissolved in dichloromethane (5 ml) under nitrogen and treated with carboethoxymethylenetriphenylphosphorane (0.67 g) at 25°. After 18 hours at 25° the solution was concentrated in vacuo and the residue washed with hexane. Combined hexane washings were concentrated in vacuo to give (±)-(2E,4E)-Ethyl-4-fluoro-5-[trans-2-(3,4-dichlorophenyl) cyclopropyl]penta-2,4-dienoate (0.58 g). NMR 1H: 7.30(1H,d), 7.00(3H,m), 6.05(1H,d), 5.90(1H,m), 4.20(2H,q), 2.00(2H,m), 1.30(3H,t), 1.30(2H,m).

Workup

  1. concentrationAfter 18 hours at 25° the solution was concentrated in vacuo
  2. washthe residue washed with hexane
  3. concentrationCombined hexane washings were concentrated in vacuo

Sources & evidence

ORD record
ord-264ca119c6d64b098aef76f65cadbfe3
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

Loading…