반응 #1077319

반응 방정식

1-[4-(methylthio)butyl]cyclopentanecarboxylic acid methyl ester

sodium hydroxide

→

1-[4-(methylthio)butyl]cyclopentanecarboxylic acid

수율 106.0%

용매

THF

methanol

반응 조건

후처리

1. 1
   온도the reaction was cooled to room temperature
2. 2
   기타The volatiles were removed under reduced pressure
3. 3
   workup.ADDITIONthe residue was diluted with water (100 mL)
4. 4
   추출was extracted with diethyl ether (2×50 mL)
5. 5
   기타to remove any neutral impurities
6. 6
   추출the mixture was extracted with ethyl acetate (2×75 mL)
7. 7
   세척The combined ethyl acetate extracts were washed with brine
8. 8
   건조dried (MgSO4)
9. 9
   여과filtered
10. 10
    농축concentrated in vacuo
11. 11
    기타the residue was dried under high vacuum

실험 절차

To a solution of 1-[4-(methylthio)butyl]cyclopentanecarboxylic acid methyl ester (18.8 mmol, 4.94 g) in a mixture of THF (38 mL) and methanol (38 mL) was added 1 N sodium hydroxide (38 mL)and the mixture was heated to 50-55° C. for 15 h. TLC analysis of the reaction mixture did not detect the presence of starting ester and the reaction was cooled to room temperature. The volatiles were removed under reduced pressure and the residue was diluted with water (100 mL) and was extracted with diethyl ether (2×50 mL) to remove any neutral impurities. Then the separated aqueous layer was acidified with 1 N hydrochloric acid and the mixture was extracted with ethyl acetate (2×75 mL). The combined ethyl acetate extracts were washed with brine, dried (MgSO4), filtered, then concentrated in vacuo and the residue was dried under high vacuum to afford 4.31 g (92%) of 1-[4-(methylthio)butyl]cyclopentanecarboxylic acid as a low melting colorless solid. HR MS: Obs. mass, 216.1181. Calcd. mass, 216.1184, M+.

출처