反応 #554570

反応方程式

Trityl chloride

14a

Methyl 6-hydroxy-hexanoate

→

orange oil 15a

収率 86.3%

Methyl 6-trityloxy-hexanoate

収率 86.3%

溶媒

pyridine

反応条件

後処理

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

実験手順

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]+.

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