Potassium Carbonate → (E)-4-(2,4-difluorophenyl)but-3-en-2-one

HRID 559283Notes

Reaction equation

HRID 559283 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.COP([CH2:17][C:18](=[O:20])[CH3:19])(=O)OC.C([O-])([O-])=O.[K+].[K+]>O>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:17]/[C:18](=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 737702,4-DifluorobenzaldehydeHCID 77872Dimethyl (2-oxopropyl)phosphonate

Product 1

HCID 58310994(E)-4-(2,4-difluorophenyl)but-3-en-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A two necked flask was charged with 2,4-difluorobenzaldehyde (4.0 g, 28.1 mmol) and (2-oxo-propyl)-phosphonic acid dimethyl ester (5.78 g, 33.0 mmol) and cooled down at 0° C. K2CO3 (7.62 g, 55.1 mmol) in H2O (14 mL) was added dropwise. Stirring was continued over night at RT. The product was extracted with EtOAc, and the organic phase was dried over Na2SO4. Flash chromatography (SiO2, Heptane/EtOAc 1:3) afforded 4.0 g (79%) of the title compound as alight yellow oil.

Workup

  1. waitwas continued over night at RT
  2. extractionThe product was extracted with EtOAc
  3. dry with materialthe organic phase was dried over Na2SO4

Sources & evidence

ORD record
ord-54f77850b0b7448d92f18ca0bbf4f00d
Source dataset
uspto-grants-2011_11
Patent number
US08063075B2

Reaction notes

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