Sodium hydride → 4-[[2-(Cyclohexyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225699노트

반응식

HRID 2225699 반응식
[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+].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH:27]1([O:33][CH2:34][CH2:35]O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>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][CH2:35][CH2:34][O:33][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:7][CH:6]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 85570p-ToluenesulfonateHCID 2247752-(Cyclohexyloxy)ethanolHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

생성물 1

HCID 543210414-[[2-(Cyclohexyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and treated with the tosylate prepared from 2-(cyclohexyloxy)ethanol (1.49 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was purified by HPLC (diethyl ether-hexane; 1:1) to provide 0.9 g of pure 4-[[2-(cyclohexyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester as an oil.

후처리

  1. extractionThe material from dichloromethane extraction
  2. customwas purified by HPLC (diethyl ether-hexane; 1:1)

출처 및 근거

ORD 기록
ord-4dd0bb32891f4f92a5c14255a7af0fa9
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05344843

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