Dimethylformamide dimethyl acetal → 3-(Dimethylamino)-1-(4-methylphenyl)-2-phenylprop-2-en-1-one

HRID 1354808Notes

Reaction equation

HRID 1354808 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH3:19][N:20]([CH3:22])[CH:21]=[C:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)=[O:16]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2280161-(4-Methylphenyl)-2-phenylethan-1-one

Product 1

HCID 672186983-(Dimethylamino)-1-(4-methylphenyl)-2-phenylprop-2-en-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-methylphenyl)-2-phenylethanone (11-1) (8.4 g, 39.95 mmol) and N,N-dimethylformamide dimethylacetal (11.9 g, 99.87 mmol) in DMF (40 mL) was heated to 100° C. for 1 h. Concentrated in vacuo to give crude 3-(dimethylamino)-1-(4-methylphenyl)-2-phenylprop-2-en-1-one (11-2) as a red oil. LRMS m/z (M+H) Calcd: 266.4, found: 266.2.

Workup

  1. concentrationConcentrated in vacuo

Sources & evidence

ORD record
ord-6b907e0722174143bbc9377224c5b7ad
Source dataset
uspto-grants-2007_05
Patent number
US07223738B2

Reaction notes

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