1-Phenyl-1,2-propanedione → 4-Dimethylamino-1-phenyl-3-butene-1,2-dione

HRID 477372Notes

Reaction equation

HRID 477372 reaction equation
[CH3:1][N:2]([CH3:12])[CH:3]=[CH:4][C:5](=[O:11])[C:6]([O:8]CC)=O.[C:13]1(C(=O)C(=O)C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OC(OCC)N(C)C)C>>[CH3:12][N:2]([CH3:1])[CH:3]=[CH:4][C:5](=[O:11])[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8]

Participants

4

Reactant 3

HCID 113631-Phenyl-1,2-propanedioneHCID 70913Dimethylformamide diethylacetalHCID 2777802Ethyl 4-(dimethylamino)-2-oxo-but-3-enoate

Product 1

HCID 545728964-Dimethylamino-1-phenyl-3-butene-1,2-dione

Procedure

The procedure is as in Example 2 for the preparation of ethyl 4-dimethylamino-2-oxo-3-butenoate, starting with 1-phenyl-1,2-propanedione (25 g) and N,N-dimethylformamide diethyl acetal (28.3 g). After purification by chromatography on a silica column with ethyl acetate as eluent, 4-dimethylamino-1-phenyl-3-butene-1,2-dione (9.3 g), m.p. 88° C., is obtained.

Workup

  1. customAfter purification by chromatography on a silica column with ethyl acetate as eluent

Sources & evidence

ORD record
ord-50a8ceb5ef524db69a48d2451b8719bd
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

Loading…