Chlorotrimethylsilane → HCID 21909109, compound

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.

1. custompartitioned with aqueous 5% NaOH (200 mL)
2. customseparated
3. extractionThe aqueous layer was extracted with Et2O
4. dry with materialthe combined organics were dried (Na2SO4)
5. filtrationfiltered
6. customevaporated

ORD record

ord-27df7348e6154e8493f7a501bf664576

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129364B2