反応 #554571

反応方程式

15a

Methyl 6-trityloxy-hexanoate

Trityl chloride

14c

Methyl-12-hydroxy-dodecanoate

→

pale yellow oil 15c

収率 40.0%

Methyl-12-trityloxy-dodecanoate

収率 40.0%

溶媒

pyridine

反応条件

後処理

1. 1
   ろ過The filtration step
2. 2
   その他instead the crude material was purified by flash column chromatography (10% EtOAc in hexanes)

実験手順

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]+.

出典