Triethylamine → 1,3-Bis(2-ethoxycarbonylethylthio)acetone

Reaction equation

Cl[CH2:2][C:3]([CH2:5]Cl)=[O:4].[SH:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C(N([CH2:20][CH3:21])CC)C>O1CCCC1>[CH2:13]([O:12][C:10]([CH2:9][CH2:8][S:7][CH2:2][C:3]([CH2:5][S:7][CH2:8][CH2:9][C:10]([O:12][CH2:20][CH3:21])=[O:11])=[O:4])=[O:11])[CH3:14]

Participants

Procedure

To a stirred solution of 1,3-dichloroacetone (6.85 g, 54 mmol) and ethyl 3-mercaptopropionate (13.9 mL, 108 mmol) in anhydrous tetrahydrofuran (150 mL) was dropwise added triethylamine (15.0 mL, 108 mmol) at 0° C. and stirred at room temperature for 24 h. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The ethyl acetate phase was washed with 5% hydrochloric acid and then brine, dried over sodium sulfate, and concentrated to dryness, affording 17.4 g of the crude 1,3-bis(2-ethoxycarbonylethylthio)acetone.