Dimethylformamide → HCID 86748110, compound

HRID 2225844Notes

Reaction equation

HRID 2225844 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:15])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10](O)=[CH:9][CH:8]=1.Cl[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)=[O:19].CN(C)C=[O:33]>>[CH3:3][O:4][C:5](=[O:15])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:33][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)=[O:19]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 2296611-(4-Tert-butylphenyl)-2-chloroethan-1-oneHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 86748110HCID 86748110, compound

Procedure

A mixture of sodium hydride (55%; 0.224 g) and 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.918 g) in dimethylformamide (12 mL) were stirred at room temperature for 30 minutes and then 2-chloro-1-[4-(1,1-dimethylethyl)phenyl]ethanone (1 g) in dimethylformamide (6 mL) was added. The reaction mixture was stirred at 60° C. overnight and worked up as in Example 20. The crude product (1.97 g) was purified initially by HPLC (ethyl acetate-hexane; 1:3) to give 0.79 g of material that was further purified by flash chromatography over silica gel (ethyl acetate-hexane-dichloromethane; 3:37:60) to afford of 0.535 g of 4-[2-[4-(1,1-dimethylethyl)phenyl-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester as an oil.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. overnight
  2. customThe crude product (1.97 g) was purified initially by HPLC (ethyl acetate-hexane; 1:3)

Sources & evidence

ORD record
ord-cb77bb529c3f479e8b773668e93c6e6e
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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