Phenol → 4-(3-Pyridylmethyl)phenoxyacetic acid ethyl ester
Reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[CH3:17][N:18]([CH3:21])C=O>>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][O:7][C:1]1[CH:6]=[CH:5][C:4]([CH2:3][C:2]2[CH:17]=[N:18][CH:21]=[CH:6][CH:1]=2)=[CH:3][CH:2]=1)[CH3:16]Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 0.70 g of the phenol compound(prepared as described in Example 9), 0.30 g of sodium hydride (content 63%) and 14 ml of N,N-dimethylformamide was stirred at 100° C. for 20 minutes, and stirred with 0.64 g of ethyl bromoacetate at 70° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water, and extracted with diethyl ether. The extract was washed with water, and a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a 0.5% V/V solution of ethanol in chloroform as eluent to give 0.166 g of the title compound having the following physical characteristics:
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in water
- extractionextracted with diethyl ether
- washThe extract was washed with water
- dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulphate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel using a 0.5% V/V solution of ethanol in chloroform as eluent
Sources & evidence
- ORD record
- ord-6c528b7701c44f04aceb9028500f958a
- Source dataset
- uspto-grants-1982_03
- Patent number
- US04317828
Reaction notes
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