Potassium Carbonate → 4-[(1E)-3-Oxo-1-buten-1-yl]benzonitrile

HRID 559287Notes

Reaction equation

HRID 559287 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.COP([CH2:17][C:18](=[O:20])[CH3:19])(=O)OC.C([O-])([O-])=O.[K+].[K+]>O>[O:20]=[C:18]([CH3:19])/[CH:17]=[CH:1]/[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660424-CyanobenzaldehydeHCID 77872Dimethyl (2-oxopropyl)phosphonate

Product 1

HCID 111267214-[(1E)-3-Oxo-1-buten-1-yl]benzonitrileYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A two necked flask was charged with 4-formyl-benzonitrile (20.0 g, 0.152 mol) and (2-oxo-propyl)-phosphonic acid dimethyl ester (30.4 g, 0.18 mol) and cooled down at 0° C. K2CO3 (42.16 g, 0.305 mol) in H2O (45 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 1:1) afforded 18.7 g (72%) of the title compound as alight yellow solid.

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-5921cd4d12dc4d85b0d4d1f154104b40
Source dataset
uspto-grants-2011_11
Patent number
US08063075B2

Reaction notes

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