反应 #2267079

ord-ea9305c7537b42d1856ce2e786c2112e

反应方程式

COc1cc2c(cc1NC(C)=O)CC(C)OC2c1ccc([N+](=O)[O-])cc1
14
COc1cc2c(cc1NC(C)=O)CC(C)OC2c1ccc([N+](=O)[O-])cc1
6-Acetylamino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman
[Na+].[OH-]
sodium hydroxide
Cl
HCl
COc1cc2c(cc1NC(C)=O)CC(C)OC2(O)c1ccc([N+](=O)[O-])cc1
22
COc1cc2c(cc1NC(C)=O)CC(C)OC2(O)c1ccc([N+](=O)[O-])cc1
6-Acetylamino-1-hydroxy-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取extracted with ethyl acetate three times
  2. 2
    洗涤The combined organic phase was washed with water
  3. 3
    干燥dried over Na2SO4
  4. 4
    其他Removal of the solvent

实验过程

A solution of 14 (1.8 g) in 5 ml of DMSO and 30 ml of DMF was cooled to 8-12° C. and air was passed through the mixture. To the solution was added 1.2 ml of 50% aqueous sodium hydroxide in one portion and the resulting mixture was stirred for 5 hours. HCl (1 N) was added, and extracted with ethyl acetate three times. The combined organic phase was washed with water, dried over Na2SO4. Removal of the solvent afforded 22 (1.9 g) as a syrup, which was used directly for the next step.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US06887867B2uspto-grants-2005_05