反应 #554570

反应方程式

Trityl chloride

14a

Methyl 6-hydroxy-hexanoate

→

orange oil 15a

收率 86.3%

Methyl 6-trityloxy-hexanoate

收率 86.3%

溶剂

pyridine

反应条件

后处理

1. 1
   其他formed
2. 2
   其他The solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe resulting material was redissolved in ice cold THF
4. 4
   其他The insoluble byproduct was removed by filtration
5. 5
   其他the filtrate was dried under reduced pressure

实验过程

Trityl chloride (18.8 g, 67.4 mmol) was added to an ice cold (0° C.) stirring solution of 14a (9.9 g, 67.4 mmol) in 80 mL of pyridine. The reaction mixture was warmed to room temperature and stirred under argon for 2 days, during which time a white byproduct formed. The solvent was removed under reduced pressure, and the resulting material was redissolved in ice cold THF. The insoluble byproduct was removed by filtration, and the filtrate was dried under reduced pressure to obtain 22.6 g (86%) of an orange oil 15a. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.43 (6H, m, p-Ar), 7.29 (6, m, m-Ar), 7.22 (3H, m, o-Ar), 3.65 (3H, s, CO2CH3), 3.05 (2H, t, 3JH—H=6.6 Hz, HO—CH2), 2.29 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.54-1.71 (4H, m, 2CH2), 1.33-1.45 (m, 2H, CH2). HRMS (EI): m/z calcd 388.2038 (C26H28O3), found 388.2039 [M]+.

来源