Reacción #554571

Ecuación de reacción

15a

Methyl 6-trityloxy-hexanoate

Trityl chloride

14c

Methyl-12-hydroxy-dodecanoate

→

pale yellow oil 15c

Rendimiento 40.0%

Methyl-12-trityloxy-dodecanoate

Rendimiento 40.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe filtration step
2. 2
   Otroinstead the crude material was purified by flash column chromatography (10% EtOAc in hexanes)

Procedimiento

The synthesis procedure of 15a was followed. Trityl chloride (1412 mg, 5.1 mmol), 14c (583 mg, 2.5 mmol), and pyridine (10 mL) were used and the reaction was prolonged to 3 days. The filtration step was omitted, instead the crude material was purified by flash column chromatography (10% EtOAc in hexanes) yielding 477 mg (40%) of a pale yellow oil 15c. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.44 (6H, m, p-Ar), 7.28 (6H, m, m-Ar), 7.21 (3H, m, o-Ar), 3.66 (3H, s, CO2CH3), 3.03 (2H, t, 3JH—H=6.6 Hz, H)—CH2), 2.29 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.55-1.65 (4H, m, 2CH2), 1.10-1.39 (14H, m, 7CH2). HRMS (EI): m/z calcd 472.2977 (C32H40O3), found 472.2968 [M]+.

Fuente