Water → HCID 18620107, compound

HRID 1862608Notes

Reaction equation

HRID 1862608 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][CH2:13][O:14][CH3:15])=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CN(C)C=O>[C:4]([C:3]1[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][O:14][CH3:15])[CH:8]=[CH:9][C:2]=1[O:1][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])#[N:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18620128HCID 18620128, compound

Product 1

HCID 18620107HCID 18620107, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-5-(2-methoxymethoxyethyl)benzonitrile (496 mg) in N,N-dimethylformamide (5 ml) were added potassium carbonate (435 mg) and ethyl bromoacetate (292 μl), and the mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, and removal of the solvent under reduced pressure gave ethyl 2-[2-cyano-4-(2-methoxymethoxyethyl)phenoxy]acetate (619 mg). To a solution of the obtained ethyl 2-[2-cyano-4-(2-methoxymethoxyethyl)phenoxy]acetate (522 mg) in ethanol (5 ml) was added concentrated hydrochloric acid (20 μl), and the mixture was stirred for 2 hours at 70° C. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, and removal of the solvent under reduced pressure gave ethyl 2-[2-cyano-4-(2-hydroxyethyl)phenoxy]acetate (449 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine, and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8f6f2847463d4fbdaf638ad7e05aa392
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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