反应 #554572

反应方程式

NaOH

15a

Methyl 6-trityloxy-hexanoate

NaOH

→

white powder 16a

收率 78.1%

6-Trityloxyhexanoic acid

收率 78.1%

溶剂

THF

water

反应条件

后处理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for another 2 days
3. 3
   其他The THF was removed under reduced pressure
4. 4
   萃取extracted with diethyl ether
5. 5
   洗涤The combined organic layers were washed with brine
6. 6
   干燥dried over MgSO4
7. 7
   其他The diethyl ether was removed under reduced pressure
8. 8
   其他the resulting crude powder was recrystalized in hexanes

实验过程

An aqueous solution of 5 M NaOH (17.5 mL, 87.5 mmol) was added to a stirring solution of 15a (20.1 g, 51.6 mmol) in 130 mL of THF and 52.5 mL of water at room temperature. After stirring for 2 days, 3.1 mL of 5 M NaOH (15.5 mmol) was added, and stirring was continued for another 2 days. The THF was removed under reduced pressure, then the aqueous residue was acidified with 1 M HCl to pH 5 and extracted with diethyl ether. The combined organic layers were washed with brine and dried over MgSO4. The diethyl ether was removed under reduced pressure, and the resulting crude powder was recrystalized in hexanes to yield 15.1 g (78%) of white powder 16a. Mp 114-116° C. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.43 (6H, m, p-Ar), 7.28 (6H, m, m-Ar), 7.22 (3H, m, o-Ar), 3.05 (2H, t, 3JH—H=6.4 Hz, HO—CH2), 2.33 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.56-1.68 (4H, m, 2CH2), 1.36-1.47 (2H, m, CH2). 13C-NMR (100 MHz, CDCl3, δH ppm): 180.26, 144.36, 128.62, 127.66, 126.79, 86.30, 63.24, 33.98, 29.63, 25.74, 24.48. HRMS (EI): m/z calcd 374.1882 (C25H26O3), found 374.1883 [M]+.

来源