Réaction #554571

Équation de réaction

15a

Methyl 6-trityloxy-hexanoate

Trityl chloride

14c

Methyl-12-hydroxy-dodecanoate

→

pale yellow oil 15c

Rendement 40.0%

Methyl-12-trityloxy-dodecanoate

Rendement 40.0%

Solvants

pyridine

Conditions de réaction

Traitement

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

Mode opératoire

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]+.

Source