1,3-Propanedithiol

• Furfural [F0073]
• 1,3-Propanedithiol [P0763]
• Chlorotrimethylsilane (= TMSCl) [C0306]
• Chloroform

Furfural (0.86 mL, 10 mmol) was dissolved in chloroform (10 mL) and cooled to 0 °C. 1,3-Propanedithiol (1.1 mL, 11 mmol) and TMSCl (0.3 mL, 2.0 mmol) were added and the reaction mixture was for 19 hours at room temperature. Ethyl acetate (30 mL) was added to the mixture and the organic layer was washed with brine (30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Purification of the crude product by silica gel chromatography (hexane:ethyl acetate = 5:1) afforded 2-(1,3-dithian-2-yl)furan (1, 1.37 g, 71% yield) as a yellow oil.

Since 1,3-propanedithiol has a foul odor, weighing, reaction, and purification were performed in a draft chamber.
The instruments and effluents were treated with sodium hypochlorite solution after the reaction.
The reaction solution was monitored by UPLC.

2-(1,3-dithian-2-yl)furan (1)

¹H NMR (400 MHz, CDCl₃); δ 7.32 (m, 1H), 6.40 (m, 1H), 6.26 (m, 1H), 5.09 (s, 1H), 2.96 (m, 4H), 2.18 (m, 1H), 2.05 (m, 1H).

• Stereocontrol with Lithium Trimethylzincate toward Gibberellin Synthesis
• M. Isobe, C.-T. Chiang, K.-W. Tsao, C.-Y. Cheng, R. Bruening, Eur. J. Org. Chem. 2012, 11, 2109.