Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Triphenylphosphine Oxide

HRID 1781374Notes

Reaction equation

HRID 1781374 reaction equation
C(N1CCC(=O)CC1)(=[O:8])C1C=CC=CC=1.COC(C=[P:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O>C1(C)C=CC=CC=1>[C:34]1([P:21](=[O:8])([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 90583N-Benzoyl-4-piperidone

Product 1

HCID 13097Triphenylphosphine OxideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under N2, a mixture of 1-benzoyl-4-piperidone (10.2 g, 0.05 mol), methyl (triphenylphosphoranylidene) acetate (25 g. 0.074 mol) in toluene (100 ml) was heated at reflux for 7 hours. After stirring at room temperature overnight, the solid was filtered off to yield 13.9 g (100%) of triphenylphosphine oxide. The mother liquor was concentrated to dryness and the residue was treated with acetic acid (42 ml), H2O, (6 ml) and 12 N HCl (6 ml). The mixture was heated at 80°-85° C. with stirring for 15 hours. The reaction was then concentrated to dryness and the residue was partitioned between saturated Na2CO3 and ethyl acetate. The aqueous layer was further extracted with ethyl acetate (1×), neutralized to pH 3 with 6 N HCl and extracted with ethylacetate (4×). The organic layer was dried, filtered and concentrated to dryness to yield 7.2 g (59%) of title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hours
  3. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-442301e70e88430aba7d194beb8dd46d
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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