Methanol → 4-({[4-(Methylsulfanyl)phenyl]sulfanyl}-methyl)bicyclo[4.1.0]heptane-3-carboxylic acid

HRID 2222908Notes

Reaction equation

HRID 2222908 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH:11]2[CH2:17][CH:16]3[CH:14]([CH2:15]3)[CH2:13][CH:12]2[C:18]([O-:20])=[O:19])=[CH:5][CH:4]=1.CO.[OH-].[Li+]>COCCOC>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH:11]2[CH2:17][CH:16]3[CH:14]([CH2:15]3)[CH2:13][CH:12]2[C:18]([OH:20])=[O:19])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 865961304-({[4-(Methylsulfanyl)phenyl]-sulfanyl}-methyl)bicyclo[4.1.0]heptane-3-carboxylate

Product 1

HCID 865961294-({[4-(Methylsulfanyl)phenyl]sulfanyl}-methyl)bicyclo[4.1.0]heptane-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl(1S/R,3R/S,4R/S,6R/S)-4-({[4-(methylsulfanyl)phenyl]-sulfanyl}-methyl)bicyclo[4.1.0]heptane-3-carboxylate was dissolved in ethylene glycol dimethyl ether (3.0 mL) and methanol (1 mL) in a 25 mL round bottom flask. Aqueous solution of lithium hydroxide (3.0 mL, 6.0 mmol, 2 M) was added and the reaction mixture was stirred at ambient temperature for 36 h. After acidification with 2 M aqueous hydrochloric acid to pH 3, the product was extracted into ether. The combined ether extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated by rotary evaporation to give (1S/R,3R/S,4R/S,6R/S)-4-({[4-(methylsulfanyl)phenyl]sulfanyl}-methyl)bicyclo[4.1.0]heptane-3-carboxylic acid.

Workup

  1. extractionAfter acidification with 2 M aqueous hydrochloric acid to pH 3, the product was extracted into ether
  2. washThe combined ether extracts were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-261755d5415a43999f19965235f7850d
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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