Water → HCID 54315383, compound

HRID 903970Notes

Reaction equation

HRID 903970 reaction equation
[OH:1][CH:2]([CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[C:3]#[N:4].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[CH2:26]([O:25][C:23]([CH2:22][O:1][CH:2]([CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[C:3]#[N:4])=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 15572607HCID 15572607, compound

Product 1

HCID 54315383HCID 54315383, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

2.69 g of 2-hydroxy-3-phenyl-3-(2-methoxy-phenoxy)-propionitrile in 25 ml of anhydrous DMA was stirred with 6.68 g of ethyl bromoacetate in the presence of 2.76 g of anhydrous potassium carbonate. The mixture was heated at 50° C. for 16 hours, poured into water and extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and concentrated to dryness, to obtain 3.55 g of 2-ethoxycarbonylmethyloxy-3-phenyl-3-(2-methoxy-phenoxy)-propionitrile (oil) (Yield 100%), which was used as such for the reaction described in the previous example.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3aead05fe8c64d2bac3d4332549f5fea
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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