Реакция #554571

Уравнение реакции

15a

Methyl 6-trityloxy-hexanoate

Trityl chloride

14c

Methyl-12-hydroxy-dodecanoate

→

pale yellow oil 15c

Выход 40.0%

Methyl-12-trityloxy-dodecanoate

Выход 40.0%

Растворители

pyridine

Условия реакции

Обработка

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

Методика

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]+.

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