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

HRID 878507Notes

Reaction equation

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

Participants

Reactant 2

HCID 114603-Methoxyacetophenone

HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 12233520(2E)-3-(dimethylamino)-1-(3-methoxyphenyl)prop-2-en-1-oneYield 89%

Procedure

The title compound was prepared in 89% yield from 1-(3-methoxyphenyl)ethanone and DMF-DMA according to the procedure for the preparation of Example 12, part A. 1H NMR (400 MHz, CDCl3): δ 2.94 (3H, s), 3.13 (3H, s), 3.85 (3H, s), 7.69 (1H, d, J=12.4 Hz), 6.98-7.01 (1H, m), 7.29-7.46 (3H, m), 7.79 (1H, d, J=12.4 Hz).

Sources & evidence

ORD record: ord-38736225182d47c195822c0d499df7a2
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987461B2

Reaction notes

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