Hydrochloric Acid → (1r/s,6r/s)-6-{[(4-Fluorophenyl)sulfanyl]methyl}cyclohex-3-ene-1-carboxylic acid

HRID 2222919Notes

Reaction equation

HRID 2222919 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH:10]2[CH:15]([C:16]([O:18]C)=[O:17])[CH2:14][CH:13]=[CH:12][CH2:11]2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>CO.COCCOC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH:10]2[CH:15]([C:16]([OH:18])=[O:17])[CH2:14][CH:13]=[CH:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 90970530Methyl(1r/s,6r/s)-6-{[(4-fluorophenyl)sulfanyl]methyl}cyclohex-3-ene-1-carboxylate

Product 1

HCID 86596137(1r/s,6r/s)-6-{[(4-Fluorophenyl)sulfanyl]methyl}cyclohex-3-ene-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of methyl(1R/S,6R/S)-6-{[(4-fluorophenyl)sulfanyl]methyl}cyclohex-3-ene-1-carboxylate (656 mg, 2.34 mmol) in methanol (1.0 ml) and ethylene glycol dimethyl ether (5.0 ml) was treated with a 2 M aqueous solution of lithium hydroxide (6.0 ml). After stirring for 19 h, the reaction mixture was adjusted to pH 2 with a 2 M aqueous solution of hydrochloric acid and partitioned between water and ethyl acetate. After separating the organic phase, the aqueous phase was extracted with an additional portion of ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. Removal of the solvent on a rotary evaporator provided (1R/S,6R/S)-6-{[(4-fluorophenyl)sulfanyl]methyl}cyclohex-3-ene-1-carboxylic acid as a golden-yellow syrup.

Workup

  1. custompartitioned between water and ethyl acetate
  2. customAfter separating the organic phase
  3. extractionthe aqueous phase was extracted with an additional portion of ethyl acetate
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. customon a rotary evaporator

Sources & evidence

ORD record
ord-b5fad359b59f4c7588f02cba87ef2b9e
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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