3-Methylacetophenone → (2E)-3-(Dimethylamino)-1-(3-methylphenyl)prop-2-en-1-one

HRID 514342

Reaction equation

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

Participants

Reactant 2

HCID 114553-Methylacetophenone

HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 19807213(2E)-3-(Dimethylamino)-1-(3-methylphenyl)prop-2-en-1-oneYield 35%

Procedure

The title compound was prepared in 35% yield from 1-(3-methylphenyl)ethanone and DMF-DMA according to the procedure for the preparation of Example 12, part A. 1H NMR (400 MHz, CDCl3): δ 2.39 (3H, s), 2.79-3.11 (6H, m), 5.70 (1H, d, J=12.4 Hz), 7.24-7.31 (2H, m), 7.66-7.71 (2H, m), 7.78 (1H, d, J=12.4 Hz).

Sources & evidence

ORD record: ord-2873005cdbc848fb862feddeea823865
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107916B2

Linked notes

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