Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate → HCID 53632560, compound

HRID 1492566Notes

Reaction equation

HRID 1492566 reaction equation
[OH:1][CH:2]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[C:18]([CH2:23][CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:20][CH2:21][CH3:22])=[O:19]>C(Cl)(Cl)Cl>[OH:1][CH:2]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:23]([CH3:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoateHCID 18950715HCID 18950715, compound

Product 1

HCID 53632560HCID 53632560, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-[2-Hydroxy-2-(3-pyridyl)ethyl]benzaldehyde (1.34 g) and (carboethoxyethylidene)triphenylphosphorane (4.28 g) were dissolved in 50 ml of chloroform, and stirred for 1.5 hours, and the solvent was distilled off under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column, and from a fraction eluted with chloroform-methanol(10:1v/v) was obtained 1.84 g of ethyl 4-[2-hydroxy-2-(3-pyridyl)ethyl]-α-methylcinnamate.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue obtained
  3. washfrom a fraction eluted with chloroform-methanol(10:1v/v)

Sources & evidence

ORD record
ord-3d93b89a4269455f947238d981ad2a82
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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