2,2-Bis-(2-phenylsulfanyl-ethyl)-malonic acid → 4-Phenylsulfanyl-2-(2-phenylsulfanyl-ethyl)-butyric acid

HRID 1830125Notes

Reaction equation

HRID 1830125 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][C:10]([CH2:17][CH2:18][S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(C(O)=O)[C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OCC)(=O)C>[C:20]1([S:19][CH2:18][CH2:17][CH:10]([CH2:9][CH2:8][S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]([OH:13])=[O:12])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 1

HCID 220539352,2-Bis-(2-phenylsulfanyl-ethyl)-malonic acid

Product 1

HCID 220540334-Phenylsulfanyl-2-(2-phenylsulfanyl-ethyl)-butyric acidYield 36.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,2-Bis-(2-phenylsulfanyl-ethyl)-malonic acid (5.628 g) was heated at 150° C. for 30 minutes. The reaction mixture was cooled to room temperature, dissolved in ethyl acetate and washed with aqueous sodium bicarbonate. The ethyl acetate solution was washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure and the residue was chromatographed on silica gel eluting with ethyl acetate/hexane to give 4-phenylsulfanyl-2-(2-phenylsulfanyl-ethyl)-butyric acid (1.831 g).

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. washThe ethyl acetate solution was washed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed by rotary evaporation at reduced pressure
  5. customthe residue was chromatographed on silica gel eluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-69426c290a3c4ecd8fd376473f6a19da
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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