Potassium Carbonate → Methyl alpha-(2-n-propyl-4-cyanophenoxy)-3,4-methylenedioxyphenylacetate

HRID 1378877Notes

Reaction equation

HRID 1378877 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[C:21]([O:23][CH3:24])=[O:22]>CC(C)=O>[CH2:10]([C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=1[O:1][CH:20]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[C:21]([O:23][CH3:24])=[O:22])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetateHCID 139876694-hydroxy-3-propylBenzonitrile

Product 1

HCID 22912470Methyl alpha-(2-n-propyl-4-cyanophenoxy)-3,4-methylenedioxyphenylacetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4.50 g (27.95 mmol) of the product of Step B in 30 mL of acetone was added 4.64 g (33.54 mmol) of powdered potassium carbonate and the reaction mixture was stirred for 10 minutes. Methyl α-bromo-3,4-methylenedioxyphenylacetate (8.01 g; 29.35 mmol) was then added and the reaction mixture refluxed overnight. The reaction mixture was cooled, filtered, and the filtrate evaporated in vacuo, dried in a vacuum to afford 10.30 g (9.87 g theoretical) of the title compound which was used without purification in the next step.

Workup

  1. temperaturethe reaction mixture refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated in vacuo
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-44a5785ccc3a4950b81c75a09ce26af1
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Reaction notes

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