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-one

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(4-chlorophenyl)ethan-1-one (3.0 g, 19.3 mmol) and N,N, dimethylformamide diisopropylacetal (20 ml) was heated at 150° C. for 16 hours. The reaction mixture was cooled to 0° C. and treated with hexanes (20 ml). The resulting solid was collected via filtration and washed with hexanes to provide the title compound: EI-MS (m/z) 209 [M+1]+.

Workup

filtrationThe resulting solid was collected via filtration
washwashed with hexanes

Sources & evidence

ORD record: ord-631ef89be47649218b1ad42fd4234d81
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429599B2

Reaction notes

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