P-Chloroacetophenone → (E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(O[CH:15](OC(C)C)[N:16]([CH3:18])[CH3:17])(C)C>>[CH3:15][N:16]([CH3:18])/[CH:17]=[CH:9]/[C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:10]

Participants

Reactant 2

HCID 7467P-Chloroacetophenone

HCID 87682N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine

Product 1

HCID 5375260(E)-1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-oneYield 99%

Procedure

A solution of 1-(4-chlorophenyl)ethane-1-one (35.0 g, 226 mmol) and N,N Dimethylformamide diisopropylacetal (35 mL) was heated to reflux for 16 hours. The reaction mixture was cooled to room temperature and treated with hexanes (50 mL). The resulting solid was collected via filtration and washed with hexanes to provide the title compound as a yellow solid (47.12 g, 99% yield): HPLC Retention Time; 6.45 min (Method B). M+1; 209.

Workup

temperatureto reflux for 16 hours
filtrationThe resulting solid was collected via filtration
washwashed with hexanes

Sources & evidence

ORD record: ord-7b143d0fd7a04fcfb5f097754da81e17
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429599B2

Reaction notes

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