반응 #1077318

반응 방정식

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

sodium hydroxide

→

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 diethyl 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
8. 8
   건조dried (MgSO4)
9. 9
   여과filtered
10. 10
    농축the solution was concentrated in vacuo
11. 11
    기타The residual material was dried under high vacuum

실험 절차

To a solution of 1-[4-(methylsulfonyl)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. After 15 h, 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 diethyl 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, dried (MgSO4), filtered and the solution was concentrated in vacuo. The residual material was dried under high vacuum to afford 4.31 g (92%) of 1-[4-(methylsulfonyl)butyl]cyclopentane carboxylic acid as a low melting colorless solid. LR MS (C11H20O4S): 249 (M+H).

출처