Sodium Hydroxide → HCID 22660091, compound

HRID 1018146Notes

Reaction equation

HRID 1018146 reaction equation
C[O:2][C:3]([C:5]1([CH2:10][CH2:11][CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>C1COCC1.CO>[CH3:17][S:14]([CH2:13][CH2:12][CH2:11][CH2:10][C:5]1([C:3]([OH:4])=[O:2])[CH2:9][CH2:8][CH2:7][CH2:6]1)(=[O:15])=[O:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22954346HCID 22954346, compound

Product 1

HCID 22660091HCID 22660091, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
52.5 °C

Procedure

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).

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was removed under vacuum
  3. additionthe residue was diluted with water (100 mL)
  4. extractionextracted with diethyl ether (2×50 mL)
  5. customto remove any neutral impurities
  6. extractionthe product was extracted with ethyl acetate (2×75 mL)
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationthe solution was concentrated in vacuo
  11. customThe residual material was dried under high vacuum

Sources & evidence

ORD record
ord-084f73a127f74ceda731ea9471463334
Source dataset
uspto-grants-2002_11
Patent number
US06479666B2

Reaction notes

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