Water → HCID 178427788, compound

Participants

Reaction Steps

p-Toluenesulfonyl chloride (3.47 g, 18.2 mmol) was added to a solution of the above preparation of (trans)-3-hydroxycyclobutanemethanol, benzoate ester (2.5 g) in dry pyridine (35 ml) under nitrogen, and the mixture was stirred at 60° for 18 hours. Water (20 ml) was added, and heating was continued for 4 hours longer. The reaction was cooled to room temperature and concentrated in vacuo to a solid, which was dissolved in ethyl acetate and water. The ethyl acetate layer was washed with water, saturated aqueous NaHCO3, and water, dried (Na2SO4), and concentrated to a solid (3.8 g). This solid was combined with 1.5 g of solid from a similar preparation. Chromatography of these solids over 200 g of LP-1 silica gel, using hexane-ethyl acetate (6:1), gave (trans)-3-[[(4-methylphenyl)sulfonyl]oxy]cyclobutanemethanol, benzoate ester containing varying amounts of its cis-isomer as shown below:

Provenance & Evidence