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

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).

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)

ORDレコード

ord-f32ec5d30eec4850a80d99d97bf82b17

出典データセット

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05114945