Dimethylformamide dimethyl acetal → 4-(Dimethylamino)-3-(4-fluorophenyl)but-3-en-2-one

HRID 30705Notes

Reaction equation

HRID 30705 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>CCCCCC>[CH3:14][N:15]([CH3:17])[CH:16]=[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:9](=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 521187(4-Fluorophenyl)acetone

Product 1

HCID 689898094-(Dimethylamino)-3-(4-fluorophenyl)but-3-en-2-oneYield 83%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(4-fluorophenyl)-2-propanone (10.0 g) and N,N-dimethylformamide dimethylacetal (8.00 g) was stirred at 120° C. for 2 hrs. The reaction mixture was cooled, and hexane was added to the precipitated solids, which were collected by filtration to give 4-(dimethylamino)-3-(4-fluorophenyl)but-3-en-2-one (11.3 g, yield 83%) as a pale-yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-483135ff7bc34f6c97c645a76cf27359
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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