Chlorotrimethylsilane → HCID 21909109, compound

Participants

Reaction Steps

Preparation of 2-furfuryl-1,3-dithiane—Furfural (40 mL, 0.4825 mol) was dissolved in CHCl3 (400 mL) and cooled to 0° C. (ice bath) with 1,3-propanedithiol (48.5 mL, 0.482 mol, 1 eq) and a catalytic amount of TMSCl (3 pipets full). The reaction mixture was allowed to warm gradually to room temperature overnight and then partitioned with aqueous 5% NaOH (200 mL) and separated. The aqueous layer was extracted with Et2O and the combined organics were dried (Na2SO4), filtered, and evaporated to afford crude furfuryl dithiane (85 g, 0.457 mol, 94.8% yield), which was taken on to the next step without further purification. 1H NMR: δ 7.38 (m, 1H), 6.40 (m, 1H), 6.35 (m, 1H), 5.23 (s, 1H, —SH), 2.97 (m, 4H), 2.19–2.10 (m, 1H), 2.05–1.94 (m, 1H). 13C NMR: δ 152.2, 142.7, 111.0, 108.3, 42.5, 30.7, 25.7.

Provenance & Evidence