Ethyl formate → 2-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile

HRID 1822759Notes

Reaction equation

HRID 1822759 reaction equation
[C:1](#[N:13])[CH2:2][C:3]1[CH:12]=[CH:11][C:8]([O:9][CH3:10])=[C:5]([O:6][CH3:7])[CH:4]=1.C[O-].[Na+].[CH:17](OCC)=[O:18]>CCOCC>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:2]([CH:17]=[O:18])[C:1]#[N:13])[CH:12]=[CH:11][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 667273,4-DimethoxybenzeneacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 164773122-(3,4-Dimethoxyphenyl)-3-oxopropanenitrileYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the mixture of homoveratronitrile (17.7 g, 0.1 mol) and sodium methoxide (7.7 g, 0.11 mol) in ether (300 mL) was added the solution of ethyl formate (8.2 mL) in ether (100 mL). The mixture was stirred vigorously for 3 days. The precipitated solid was filtered, washed with ether. The solid was dissolved in water (100 mL). After adding 10% acetic acid to pH=3, the resulting precipitation was collected by filtration, washed with water and dried to afford 2-(3,4-dimethoxy phenyl)-3-oxo-propionitrile as white solid (19 g, 93%). LC-MS m/e calcd for C11H11NO3 (MH+) 206. found 206.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with ether
  3. dissolutionThe solid was dissolved in water (100 mL)
  4. additionAfter adding 10% acetic acid to pH=3
  5. customthe resulting precipitation
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-b536feda547147abbd0b62660a92a7e3
Source dataset
uspto-grants-2006_05
Patent number
US07037924B2

Reaction notes

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