4-Methylbenzenethiol → HCID 12922226, compound

Participants

Reaction Steps

A 100 ml flask was flame dried, purged with dry nitrogen and fitted with a magnetic stirrer, heating mantle and condenser. Dry THF (25 ml), t-butanol (25 ml), potassium t-butoxide (0.700 g, 2.5 equiv.) and 4-methylthiophenol (1.0515 g, 3.0 equiv.) were added and the mixture was allowed to stir until all of the added solid had dissolved. 1,(R,S),2,(S,R),4(R,S),4(R,S),5(R,S)-4,5-bis((dipropylcarbamoyl-methoxy)-4-oxa-[4.1.0]-bicycloheptane (1.030 g, 2.50 mmol) was added and the mixture was warmed and allowed to reflux for 72 hours. The reaction vessel was cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in diethyl ether and extracted 4 times with saturated sodium carbonate and once with brine. The organic layer was dried over sodium sulfate, filtered and the solvent was removed in vacuo. Pure product F was obtained by column chromatography of the residue with 100% ethyl acetate yielding pure 1,(R,S),2(R,S),4(R,S),5(R,S)-4,5-bis(dipropylcarbamoyl)-methoxy)- 2-(4-methyl thiophenoxy)-cyclohexanol, subreaction product 15, (0.423 g, 31%) as a viscous oil.

Provenance & Evidence