反应 #2559

ord-cbf5b75d0c184a8f8de856d128b7a42f

反应方程式

COc1cccc(C(=O)N(CCOC2CCCCO2)c2ccccc2OC)c1
3-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamide
Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulfonic acid monohydrate
O=C([O-])O.[Na+]
sodium bicarbonate
COc1cccc(C(=O)N(CCO)c2ccccc2OC)c1
title compound
收率 86.8%
COc1cccc(C(=O)N(CCO)c2ccccc2OC)c1
N-(2-Hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamide
收率 86.8%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取extracted with ether
  2. 2
    洗涤washed with water and saturated brine
  3. 3
    干燥The resulting organic layer was dried on anhydrous magnesium sulfate
  4. 4
    其他the solvent was removed by evaporation
  5. 5
    其他the resulting colorless oily residue was purified

实验过程

3-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamide (501 mg, 1.30 mmol) was dissolved in methanol (4 ml) to which was subsequently added a catalytically effective amount of p-toluenesulfonic acid monohydrate and stirred for 3 hours at room temperature. The reaction solution was mixed with saturated sodium bicarbonate aqueous solution (10 ml) and extracted with ether, and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous magnesium sulfate, the solvent was removed by evaporation and then the resulting colorless oily residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=3:1) to obtain 340 mg (86.8%) of the title compound in the form of light yellow oil.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US05728835uspto-grants-1998_03