반응 #554572

반응 방정식

NaOH

15a

Methyl 6-trityloxy-hexanoate

NaOH

→

white powder 16a

수율 78.1%

6-Trityloxyhexanoic acid

수율 78.1%

용매

THF

water

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for another 2 days
3. 3
   기타The THF was removed under reduced pressure
4. 4
   추출extracted with diethyl ether
5. 5
   세척The combined organic layers were washed with brine
6. 6
   건조dried over MgSO4
7. 7
   기타The diethyl ether was removed under reduced pressure
8. 8
   기타the resulting crude powder was recrystalized in hexanes

실험 절차

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]+.

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