Monobenzone → Benzene, (hexyloxy)-

Participants

Reaction Steps

To a three-neck flask flushed with argon and fitted with a magnetic stir bar was added 30 ml of dry THF, 1.379 gm (6.9 mmol) of p-benzyloxyphenol (the compound of Formula IV), 0.8 gm (6.9 mmol) of (2S,3S)-3-prophloxiranemethanol (the compound of Formula V), and 1.98 gm (7.59 mmol) of triphenylphosophine. The resulting solution was heated to reflux and 1.2 ml (1.32 gm, 7.59 mmol) of diethyl azodicarboxylate was added over a period of 7 hr. After the addition was complete the reaction mixture was allowed to cool to room temperature and stir for an additional two days under argon. The solvent was then removed, and the residue purified by flash chromatography on silica gel using 85:15 hexanes/ethyl acetate as eluent. In this manner 1.6 gm (78%) of 4-benzyloxy-1-[2S,3S)-epoxy]-hexyloxybenzene (the compound of Formula VI) was obtained.

Provenance & Evidence