p-METHYLACETOPHENONE → (2E)-3-(dimethylamino)-1-(4-methylphenyl)prop-2-en-1-one

HRID 514339Notes

Reaction equation

HRID 514339 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH:14](OC)OC)[CH3:13]>>[CH3:11][N:12]([CH3:14])/[CH:13]=[CH:9]/[C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:10]

Participants

3

Reactant 2

HCID 8500p-METHYLACETOPHENONEHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5398494(2E)-3-(dimethylamino)-1-(4-methylphenyl)prop-2-en-1-oneYield 74%

Procedure

A solution of 1-(4-methylphenyl)ethanone (1.34 g, 10 mmol) in DMF-DMA (10 mL) was stirred at 100° C. overnight. The reaction mixture was cooled, concentrated, and purified by flash column chromatography (PE/EA=4:1˜2:1) to give the title compound (1.40 g, 74%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 2.37 (3H, s), 2.95-3.11 (6H, m), 6.72 (1H, d, J=12.0 Hz), 7.21 (2H, d, J=8.0 Hz), 7.78-7.82 (m, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. custompurified by flash column chromatography (PE/EA=4:1˜2:1)

Sources & evidence

ORD record
ord-84fe089ec59c409aad7f3b51d7e53f6a
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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