1-Propene, 1,1-diethoxy- → methyl trans-4-acetylamino-2,2-diethoxy-3,6-dimethyl-3,4-dihydro-2H-pyran-5-carboxylate

HRID 466278Notes

Reaction equation

HRID 466278 reaction equation
[CH2:1]([O:3][C:4]([O:7][CH2:8][CH3:9])=[CH:5][CH3:6])[CH3:2].[CH3:10][O:11][C:12](=[O:22])[C:13](=[CH:17][NH:18][C:19](=[O:21])[CH3:20])[C:14](=[O:16])[CH3:15]>C1(C)C=CC=CC=1>[C:19]([NH:18][C@@H:17]1[C:13]([C:12]([O:11][CH3:10])=[O:22])=[C:14]([CH3:15])[O:16][C:4]([O:7][CH2:8][CH3:9])([O:3][CH2:1][CH3:2])[C@H:5]1[CH3:6])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 1408411-Propene, 1,1-diethoxy-HCID 178500808HCID 178500808, compound

Product 1

HCID 67850473methyl trans-4-acetylamino-2,2-diethoxy-3,6-dimethyl-3,4-dihydro-2H-pyran-5-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,1-Diethoxyprop-1-ene (5.0 ml) was added in one portion to a stirred solution of methyl-2-acetylaminomethylene-3-oxobutanoate (5.2 g) in toluene (15 ml) at 20°-25° C. An exothermic reaction ensued and a crystalline solid precipitated out. The reaction mixture was stirred for 2 further hours at ambient temperature and the solid was then filtered off to give methyl trans-4-acetylamino-2,2-diethoxy-3,6-dimethyl-3,4-dihydro-2H-pyran-5-carboxylate (4.0 g), m.p. 152°-154° C. The structure of this ester was ascertained using X-ray analysis. The n.m.r. spectrum in deuterochloroform showed a signal for the --CH(N)--proton at 4.85 ppm (doublet of doublets of quartets, J3,4 =1.5, J4,NH =9.8, J4,7 =0.9 Hz, C6Me=C7).

Workup

  1. customAn exothermic reaction
  2. customa crystalline solid precipitated out
  3. filtrationthe solid was then filtered off

Sources & evidence

ORD record
ord-e182555e96604bb9a4bdd27d52e549d2
Source dataset
uspto-grants-1992_10
Patent number
US05155236

Reaction notes

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