Hexane → HCID 19783086, compound

Reaction equation

[F:1][C:2]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1.CCCCCC>C1(C)C=CC=CC=1>[F:1][C:2]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH2:6][CH2:5][CH:4]=[C:3]1[SH:23]

Participants

Procedure

Referring to the process described in Bulletin des Societe Chimiques Belges volume 87, page 223 (1978), 5.4 g (30 mmol) of ethyl 1-fluoro-2-oxocyclohexanecarboxylate was dissolved in 50 ml of toluene, to this was added 6.0 g (15 mmol) of Lawesson's reagent, and reaction was carried out at 100° C. for 5 hours. 100 ml of hexane was added, the precipitate was filtered out and the solvent was distilled away. The filtrate was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate=15/1) to obtain 1.1 g (yield: 18 % of ethyl 1-fluoro-2-mercapto-2-cyclohexenecarboxylate.