4'-Methoxyacetophenone → (2E)-3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-one

HRID 514353Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[CH3:12][N:13]([CH:15](OC)OC)[CH3:14]>>[CH3:12][N:13]([CH3:15])/[CH:14]=[CH:10]/[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:11]

Participants

Reactant 2

HCID 74764'-Methoxyacetophenone

HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5397461(2E)-3-(dimethylamino)-1-(4-methoxyphenyl)prop-2-en-1-oneYield 88%

Procedure

The title compound was prepared in 88% yield from 1-(4-methoxyphenyl)ethanone and DMF-DMA according to the procedure for the preparation of Example 12, part A. 1H NMR (400 MHz, CDCl3): δ 2.88-3.06 (6H, br s), 3.85 (3H, s), 5.71 (1H, d, J=12.0 Hz), 6.91 (2H, d, J=8.8 Hz), 7.84 (1H, d, J=12.0 Hz), 7.91 (2H, d, J=8.8 Hz).

Sources & evidence

ORD record: ord-5aa013ad1703493197f77f9d568a5352
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107916B2

Reaction notes

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