Diethyl Malonate → 2,2-Bis-(2-phenylsulfanyl-ethyl)-malonic acid diethyl ester

HRID 1830123Notes

Reaction equation

I[CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:11]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:20]([O:19][C:11](=[O:18])[C:12]([CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:21]

Participants

Conditions

Temperature: 52 °C

Procedure

A mixture of 2-iodoethylphenyl sulfide (19.81 g, 75 mmol), diethyl malonate (4.80 g, 30 mmol), potassium carbonate (10.35 g, 75 mmol) and DMF (40 mL) was heated at 52° C. for 18 hours. More potassium carbonate (10 g) was added and the reaction was continued at 52° C. for another 8 hours. The reaction mixture was cooled, diluted with ice water and the product extracted with ethyl acetate. The extracts were 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 2,2-bis-(2-phenylsulfanyl-ethyl)-malonic acid diethyl ester (5.648 g).

Workup

temperatureThe reaction mixture was cooled
extractionthe product extracted with ethyl acetate
washThe extracts were washed with saturated aqueous sodium chloride
dry with materialdried over magnesium sulfate
customThe solvent was removed by rotary evaporation at reduced pressure
customthe residue was chromatographed on silica gel eluting with ethyl acetate/hexane

Sources & evidence

ORD record: ord-ec49d261e4ba4dca99ee4de51b62dcc3
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064123B1

Reaction notes

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