Sodium hydride → 4-[2-(1-Naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225842Notes

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]([OH:13])=[CH:9][CH:8]=1.Cl[CH2:17][C:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19]>CN(C)C=O>[CH3:3][O:4][C:5](=[O:15])[C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)=[O:19])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (55%; 0.238 g) and 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.978 g) in dimethylformamide (12 mL) were stirred at room temperature for 30 minutes and then 2-chloro-1-(1-naphthalenyl)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 (1.7 g) was purified by flash chromatography over silica gel (ethyl acetate-hexane-dichloromethane; 2.5:37.5:60) to afford of 0.277 g of 4-[2-(1 -naphthalenyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester. Crystallization of the ester from ethyl acetate-hexane gave the analytical specimen, mp 99°-100.5° C.

Workup

customThe crude product (1.7 g) was purified by flash chromatography over silica gel (ethyl acetate-hexane-dichloromethane; 2.5:37.5:60)

Sources & evidence

ORD record: ord-0f6e4097522443a79b4ae2e9755d662d
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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