반응 #554570

반응 방정식

Trityl chloride

14a

Methyl 6-hydroxy-hexanoate

→

orange oil 15a

수율 86.3%

Methyl 6-trityloxy-hexanoate

수율 86.3%

용매

pyridine

반응 조건

후처리

1. 1
   기타formed
2. 2
   기타The solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe resulting material was redissolved in ice cold THF
4. 4
   기타The insoluble byproduct was removed by filtration
5. 5
   기타the filtrate was dried under reduced pressure

실험 절차

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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