Ethyl 2-(triphenylphosphoranylidene)propionate → HCID 53707784, compound

HRID 1105629Notes

Reaction equation

HRID 1105629 reaction equation
C1[O:15][C:4]([CH3:14])([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][CH:7]=2)OC1.[C:16]([C:21](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:22])([O:18][CH2:19][CH3:20])=[O:17]>O1CCCC1>[C:16]([C:21]([CH3:22])=[CH:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4](=[O:15])[CH3:14])=[CH:11][CH:10]=1)([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 79792Ethyl 2-(triphenylphosphoranylidene)propionateHCID 86010588HCID 86010588, compound

Product 1

HCID 53707784HCID 53707784, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-formylphenylpropan-2-one-2-ethylene acetal (3.11 g) and 1-carboethoxyethylidenetriphenylphosphorane (5.47 g) was refluxed in tetrahydrofuran under nitrogen for 1 h. The solvent was evaporated and the residue chromatographed on alumina (200 g). Elution with dichloromethane gave the title compound as the ethylene acetal (1.7 g). This was dissolved in ethanol-2 N hydrochloric acid and stirred at ambient temperature until tlc showed no acetal present. The aqueous was extracted with ether (3×50 ml) and the combined ether layers washed with water (×2), sodium bicarbonate solution, and dried (MgSO4). Removal of the solvent gave the title compound (1.05 g). τ(CDCl3) 8.7 (3H, t, 3=7 Hz), 7.92 (3H, s), 7.9 (3H, s), 6.35 (2H, s), 5.8 (2H, q, J=7 Hz), 2.8 (2H, d, J=8 Hz), 2.6 (2H, d, J=8 Hz), 2.35 (1H, broad s).

Workup

  1. customThe solvent was evaporated
  2. customthe residue chromatographed on alumina (200 g)
  3. washElution with dichloromethane

Sources & evidence

ORD record
ord-a2895aa41cc44fc7b60784ea5e1fcf9f
Source dataset
uspto-grants-1982_01
Patent number
US04309443

Reaction notes

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