Sodium hydride → 4-[3-[3-Hydroxy-4-(methoxycarbonyl)-2-propylphenoxy) propoxy]-alpha-oxobenzeneacetic acid ethyl ester

HRID 2225831Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:2].[H-].[Na+].[CH3:17][O:18][C:19](=[O:35])[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29]Br)=[C:22]([CH2:31][CH2:32][CH3:33])[C:21]=1[OH:34]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:29][CH2:28][CH2:27][O:26][C:23]2[CH:24]=[CH:25][C:20]([C:19]([O:18][CH3:17])=[O:35])=[C:21]([OH:34])[C:22]=2[CH2:31][CH2:32][CH3:33])=[CH:8][CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.47 g) and 55% sodium hydride (0.116 g) in dimethylformamide (10 mL) was stirred for 15 minutes and then treated with 4-(3-bromopropoxy)-2-hydroxy-3-propylbenzoic acid methyl ester (0.8 g) in dimethylforrnamide (5 mL). The mixture was heated at 50° C. for 20 hours and worked up as in Example 20. The residual oil was purified by flash chromatography over silica gel (ethyl acetate-hexane; 3:17) and then was crystallized from hexane to give 0.6 g of 4-[3-[3-hydroxy-4-(methoxycarbonyl)-2-propylphenoxy) propoxy]-alpha-oxobenzeneacetic acid ethyl ester, mp 62°-64° C.

Workup

customThe residual oil was purified by flash chromatography over silica gel (ethyl acetate-hexane; 3:17)
customwas crystallized from hexane

Sources & evidence

ORD record: ord-48a6585da03641e98465a9b687452b43
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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