Реакция #554573

Уравнение реакции

NaOH

15b

Methyl-9-trityloxy-nonanoate

→

pale yellow oil 16b

Выход 93.0%

9-Trityloxy-nonanoic acid

Выход 93.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   Другоеthe solvent was removed by rotary evaporation
2. 2
   ДругоеThe purification

Методика

Aqueous 0.5 M NaOH (13.2 mL, 6.6 mmol) was added to a stirring solution of 15b (1.41 g, 3.3 mol) in 25 mL of THF. The reaction mixture was stirred for 3 days at room temperature, and then the solvent was removed by rotary evaporation. The purification was carried out by flash column chromatography (gradient 10% EtOAc in hexanes to 100% EtOAc) to obtain 1.28 g (93%) of a pale yellow oil 16b. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.43 (6H, m, p-Ar), 7.28 (6H, m, m-Ar), 7.21 (3H, m, o-Ar), 3.03 (2H, t, 3JH—H=6.6 Hz, HO—CH2), 2.33 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.56-1.66 (4H, m, 2CH2), 1.20-1.40 (8H, m, 4CH2). 13C-NMR (100 MHz, CDCl3, δH ppm): 180.26, 144.46, 128.63, 127.64, 126.74, 86.22, 63.55, 34.04, 29.95, 29.24, 29.13, 28.96, 26.15, 24.60. HRMS (EI): m/z calcd 416.2351 (C28H32O3), found 416.2360 [M]+.

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