Ethyl bromoacetate → 4-(3-Pyridylmethyl)phenoxyacetic acid ethyl ester

HRID 1680031Notes

Reaction equation

Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1.[H-].[Na+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)=[CH:10][CH:11]=1)[CH3:24]

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-35306f858dae4529927e9e023bb33a92
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04271170

Reaction notes

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