Sodium hydride → HCID 19004519, compound

HRID 2225738Notes

Reaction equation

HRID 2225738 reaction equation
C[O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].Cl[CH2:17][C:18]1[O:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[CH:22]=1>CN(C)C=O.O>[O:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[CH:22]=[C:18]1[CH2:17][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:12])[C:3]([OH:2])=[O:13])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1843482-ChloromethylbenzofuranHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 19004519HCID 19004519, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.52 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.405 g), stirred for 10 minutes and treated with 2-chloromethylbenzofuran (1.4 g). The mixture was stirred at room temperature under argon for 3 hours, diluted with water, and extracted with ethyl acetate. Evaporation of the organic extracts provided crude methyl ester as a liquid. Treatment of a portion of this ester (1.02 g) with potassium hydroxide (0.18 g) in a methanol-water mixture, followed by acidification of the mixture with hydrochloric acid and filtration provided 4-[[2-benzofuranyl)methoxy]-alpha-oxobenzeneacetic acid as a white solid, mp 120° C.

Workup

  1. stirringThe mixture was stirred at room temperature under argon for 3 hours
  2. extractionextracted with ethyl acetate
  3. customEvaporation of the organic extracts
  4. customprovided crude methyl ester as a liquid
  5. filtrationTreatment of a portion of this ester (1.02 g) with potassium hydroxide (0.18 g) in a methanol-water mixture, followed by acidification of the mixture with hydrochloric acid and filtration

Sources & evidence

ORD record
ord-ec6d9da81ce943b9b1c9bad290dcd535
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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