Water → HCID 66578066, compound

HRID 533555Notes

Reaction equation

HRID 533555 reaction equation
[CH3:1][C:2]([S:23]([CH3:26])(=[O:25])=[O:24])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)[C:3]([O:5]CC)=[O:4].O.[OH-].[Li+].O>O1CCCC1.CO.Cl>[CH3:1][C:2]([S:23]([CH3:26])(=[O:24])=[O:25])([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66577949HCID 66577949, compound

Product 1

HCID 66578066HCID 66578066, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methyl-2-(methylsulfonyl)-4-[4-(phenylthio)phenyl]butanoate (348.6 mg, 0.887 mmol) in tetrahydrofuran/methanol (4:1, 10 mL) was added a solution of lithium hydroxide monohydrate in water (1.78 M, 3.55 mmol). The mixture was stirred at ambient temperature overnight. The mixture was diluted with aqueous HCl (1N in water) and extracted with diethyl ether 2×. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated to dryness to afford 2-methyl-2-(methylsulfonyl)-4-[4-(phenylthio)phenyl]butanoic acid as a solid. 323 mg. LCMS: (M−1) 363.3.

Workup

  1. extractionextracted with diethyl ether 2×
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-947b91750e1a49bf8f575f4d2a47d93d
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

Loading…