Reacción #554570

Ecuación de reacción

Trityl chloride

14a

Methyl 6-hydroxy-hexanoate

→

orange oil 15a

Rendimiento 86.3%

Methyl 6-trityloxy-hexanoate

Rendimiento 86.3%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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]+.

Fuente