반응 #1369807

반응 방정식

1-[4-(methylsulfonyl)butyl]cyclopentane carboxylic acid methyl ester

sodium hydroxide

→

title compound

수율 92.3%

1-[4-(Methylsulfonyl)butyl]cyclopentane Carboxylic Acid

수율 92.3%

용매

THF

methanol

반응 조건

후처리

1. 1
   온도to cool to room temperature
2. 2
   기타The solvent was removed under vacuum
3. 3
   workup.ADDITIONthe residue was diluted with water (100 mL)
4. 4
   추출extracted with ether (2×50 mL)
5. 5
   기타to remove any neutral impurities
6. 6
   추출the product was extracted with ethyl acetate (2×75 mL)
7. 7
   세척The combined extracts were washed with brine solution
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   여과After filtration of the drying agent
10. 10
    농축the solution was concentrated under vacuum
11. 11
    기타the residue was dried under high vacuum

실험 절차

To a solution of 1-[4-(methylsulfonyl)butyl]cyclopentane carboxylic 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). The mixture was heated to 50-55° C. for 15 h at which point TLC analysis of the reaction mixture indicated the absence of starting material and the mixture was allowed to cool to room temperature. The solvent was removed under vacuum and the residue was diluted with water (100 mL) and extracted with ether (2×50 mL) to remove any neutral impurities. Then, the basic aqueous layer was acidified with 1 N hydrochloric acid and the product was extracted with ethyl acetate (2×75 mL). The combined extracts were washed with brine solution and dried over anhydrous sodium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the residue was dried under high vacuum to afford 4.31 g (92%) of the title compound as a low melting white solid. LR MS (C11H20O4S): 249 (M+H).

출처