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

HRID 487756Notes

Reaction equation

HRID 487756 reaction equation
[CH2:1]([O:3][C:4]([O:7][CH2:8][CH3:9])=[CH:5][CH3:6])[CH3:2].[C:10]([NH:13][CH:14]=[C:15]([C:20](=[O:22])[CH3:21])[C:16]([O:18][CH3:19])=[O:17])(=[O:12])[CH3:11]>C1(C)C=CC=CC=1>[C:10]([NH:13][C@@H:14]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:20]([CH3:21])[O:22][C:4]([O:7][CH2:8][CH3:9])([O:3][CH2:1][CH3:2])[C@H:5]1[CH3:6])(=[O:12])[CH3:11]

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 (1.0 ml) was added to a solution of methyl 2-acetylaminomethylene-3-oxobutanoate (1.0 g) and tris (6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octandionato)ytterbium (0.05 g) in toluene (3.0 ml) at 20° C. After stirring for 2 hr at ambient temperature, the reaction mixture was filtered to give methyl trans-4-acetylamino-2,2-diethoxy-3,6-dimethyl-3,4-dihydro-2H-pyran-5-carboxylate (1.05 g), m.p. 153°-4° C.

Workup

  1. customat 20° C
  2. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-d4e593e280ed4936a19aca20574bbd07
Source dataset
uspto-grants-1994_03
Patent number
US05296613

Reaction notes

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