p-Toluenesulfonic acid → Triphenylphosphine Oxide

HRID 1252628Notes

Reaction equation

HRID 1252628 reaction equation
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.O[CH:13]([C:16]1[NH:17][CH:18]=[C:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20](=[O:22])[CH:21]=1)OC.[C:31]([CH:36]=[P:37]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([O:33][CH2:34][CH3:35])=[O:32]>O1CCOCC1>[O:22]=[C:20]1[C:19]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:18][NH:17][C:16]([CH:13]=[CH:36][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:21]1.[C:50]1([P:37](=[O:8])([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 141825172-(1-hydroxy-1-methoxymethyl)-5-(phenylmethoxy)-4(1H)-pyridinone

Product 2

HCID 13097Triphenylphosphine OxideHCID 867421683-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinyl]-2-propenoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.5 g of p-toluenesulfonic acid, 6.26 g of 2-(1-hydroxy-1-methoxymethyl)-5-(phenylmethoxy)-4(1H)-pyridinone and 8.35 g of carbethoxymethylenetriphenylphosphorane were stirred for 3 hours in 100 ml of dioxane at 70° C. A clear, dark-colored solution was formed. Evaporation of the solvent in vacuo yielded an oily residue of the title compound and triphenylphosphine oxide. The residue was dissolved in 30 ml of isopropanol and crystals of product began to separate. After standing in a refrigerator overnight, the crystals were filtered off, washed with ether and recrystallized from isopropanol. Yield: 5.72 g, melting point 188° C.

Workup

  1. customA clear, dark-colored solution was formed
  2. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-a908bb603e0146ed9a83ce1678d4b7aa
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

Loading…