Sodium hydride → HCID 54524851, compound

HRID 2225847Notes

Reaction equation

HRID 2225847 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:16])[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH3:4].Cl[CH2:18][C:19]([CH:21]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20]>CN(C)C=O>[CH2:3]([O:5][C:6](=[O:16])[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:18][C:19]([CH:21]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])=[CH:10][CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 190044992-Chloro-1-cyclooctylethan-1-one

Product 1

HCID 54524851HCID 54524851, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

55% Sodium hydride (0.14 g) was stirred with 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.622 g) in dimethylformamide (8 mL) under argon for 30 minutes and then the solution was treated with 2-chloro-1-cyclooctylethanone (0.53 g) in dimethylformamide (3 mL). The mixture, stirred at room temperature overnight and the at 60° C. for 1 hour, was worked up as in Example 20. The residual oil was purified by flash chromatography over silica gel (3% ethyl acetate in dichloromethane-hexane 1:1 ) to provide of 0.399 g of 4-(2-cyclooctyl-2-oxoethoxy)-alpha-oxobenzeneacetic acid ethyl ester as an oil.

Workup

  1. waitthe at 60° C. for 1 hour
  2. customThe residual oil was purified by flash chromatography over silica gel (3% ethyl acetate in dichloromethane-hexane 1:1 )

Sources & evidence

ORD record
ord-ae344ec58ce64e0c809e18b7cdf230df
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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