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

HRID 1869270Notes

Reaction equation

HRID 1869270 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

The solution of 1-(4-methylphenyl)-2-phenylethanone (1-1) (Renault, O; Dallemagne, P.; and Rault, S. Org. Prep. Proced. Int. 1999, 31, 324) (3.29 g, 15.65 mmol) and N,N-dimethylformamide dimethylacetal (4.66 g, 39.12 mmol) in DMF (15 mL) was stirred at 110° C. for 1 h. The mixture was concentrated in vacuo to give 3-(dimethylamino)-1-(4-methylphenyl)-2-phenylprop-2-en-1-one (1-2. LRMS m/z (M+H) Calcd: 266.4, found: 266.2.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-544963cce72046beb6a601f042bf7f9d
Source dataset
uspto-grants-2009_12
Patent number
US07638530B2

Reaction notes

Loading…