Acetic acid, 2-oxo-, methyl ester → 2-Methyl 1-(phenylmethyl) 3,4-dihydro-4-oxo-1,2(2H)-pyridinedicarboxylate

HRID 1196504Notes

Reaction equation

HRID 1196504 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=O.C1(P(=[N:26][C:27](=[O:36])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO[CH:39]=[CH:40][C:41]([O:43][Si](C)(C)C)=[CH2:42]>C1C=CC=CC=1>[O:43]=[C:41]1[CH:40]=[CH:39][N:26]([C:27]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:36])[CH:2]([C:1]([O:5][CH3:6])=[O:4])[CH2:42]1

Participants

5

Reactant 3

HCID 70205Acetic acid, 2-oxo-, methyl esterHCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadieneHCID 10916618benzyl N-(triphenyl-lambda5-phosphanylidene)carbamate

Product 1

HCID 151232422-Methyl 1-(phenylmethyl) 3,4-dihydro-4-oxo-1,2(2H)-pyridinedicarboxylateYield 70.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of methyl glyoxylate (1.92 g) and (phenylmethyl) (triphenylphosphoranylidene)carbamate (6.00 g) in benzene (100 ml), was stirred at reflux under nitrogen, for 1 h. A solution of 1-methoxy-3-trimethylsilyloxybutadiene (5.00 g) in benzene (40 ml) was added and the resulting solution stirred at reflux, under nitrogen, for 18 h. The benzene was evaporated in vacuo, and the residue dissolved in tetrahydrofuran (100 ml), treated with 1M hydrochloric acid (10 ml) and stirred at 22° for 1 h. The solution was diluted with ethyl acetate (100 ml), water (40 ml) and the aqueous phase separated. The organic phase was washed with saturated aqueous sodium chloride, dried and evaporated. The residue was purified by chromatography eluting with ethyl acetate-hexane (1:1) to give the title compound as an oil (2.97 g).

Workup

  1. temperatureat reflux under nitrogen, for 1 h
  2. temperatureat reflux, under nitrogen, for 18 h
  3. customThe benzene was evaporated in vacuo
  4. dissolutionthe residue dissolved in tetrahydrofuran (100 ml)
  5. additiontreated with 1M hydrochloric acid (10 ml)
  6. stirringstirred at 22° for 1 h
  7. additionThe solution was diluted with ethyl acetate (100 ml), water (40 ml)
  8. customthe aqueous phase separated
  9. washThe organic phase was washed with saturated aqueous sodium chloride
  10. customdried
  11. customevaporated
  12. customThe residue was purified by chromatography
  13. washeluting with ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-f32ec5d30eec4850a80d99d97bf82b17
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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