Sodium hydride → 4-[2-[[1,1'-Biphenyl]-2-yl]-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225845Notes

Reaction equation

HRID 2225845 reaction equation
[CH3:1][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+].[C:16]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:25])[CH2:23]Br>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:23][C:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 127478451-([1,1'-Biphenyl]-2-yl)-2-bromoethan-1-one

Product 1

HCID 539437794-[2-[[1,1'-Biphenyl]-2-yl]-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl esterYield 41.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.721 g) in dimethylformamide (8 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 30 minutes and then 1-[1,1'-biphenyl]-2-yl-2-bromoethanone (1.1 g) in dimethylformamide (4 mL). The mixture was stirred at room temperature overnight and worked up as in Example 20. The residual oil (1.5 g) was purified by flash chromatography over silica gel (dichloromethane) to afford of 0.62 g of 4-[2-[[1,1'-biphenyl]-2-yl]-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe residual oil (1.5 g) was purified by flash chromatography over silica gel (dichloromethane)

Sources & evidence

ORD record
ord-381719996dc64f48bf5776250ca76c95
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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