p-Toluenesulfonic acid → Triphenylphosphine Oxide

HRID 4116

Reaction equation

HRID 4116 reaction equation
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.[O:12]=[C:13]1[C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][NH:16][C:15]([CH:27](O)OC)=[CH:14]1.[CH2:31]([O:33][C:34](=[O:55])[CH:35]=[P:36]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:32]>>[O:12]=[C:13]1[C:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][NH:16][C:15](/[CH:27]=[CH:35]/[C:34]([O:33][CH2:31][CH3:32])=[O:55])=[CH:14]1.[C:49]1([P:36](=[O:8])([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

5

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 14182518(E)-3-[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinyl]-2-propenoic acid, ethyl ester

Procedure

p-Toluenesulfonic acid (0.5 g), 6.26 g of 1,4-dihydro-4-oxo-2-[(hydroxy)(methoxy)methyl]-5-(phenylmethoxy)pyridine and 8.35 g of (triphenylphosphoranylidene)acetic acid ethyl ester were stirred for three hours at 70° C. A clear dark solution was formed. Evaporation of the solvent in vacuo yielded an oily residue of the title compound and triphenylphosphine oxide. This was dissolved in 30 ml of isopropanol. After standing overnight in a refrigerator, the resulting crystals were filtered off, washed with ether and recrystallized from isopropanol (yield: 5.72 g).

Workup

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

Sources & evidence

ORD record
ord-412af217645140608f36a96b6d5ec195
Source dataset
uspto-grants-1988_02
Patent number
US04723002

Linked notes

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