Benzoyl chloride → HCID 18534541, compound

Participants

Reaction Steps

The ter-cyclopentane tetra-ol (0.75 g, 1.25 mmol) was dissolved into 0.1 M THF at room temperature. Added benzoyl chloride (0.88 ml, 7.55 mmol) to the tetra-ol solution, and stirred at room temperature for 5 min, before adding Et3N (1.08 ml, 7.75 mmol). After stirring at room temperature for 10 min, reaction became slightly cloudy. After stirring for 24 hr at room temperature, reaction was diluted with ethyl acetate and poured into water (20 ml). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3×20 ml). The organic extracts were pooled, and washed sequentially with 10% aq HCl solution (10 ml), water (10 ml), and sat aq Na2CO3 (10 ml). The layers were separated and the organic layer was dried over Na2SO4, filtered, and reduced in vacuo to afford a golden yellow residue. Purification of the residue via flash chromatography (silica, 75:25 hexanes:ethyl acetate) afforded the ter-cyclopentane hexa-benzoate (0.76 mg, 60% yield) as an off-white solid.

Provenance & Evidence