Triethylamine → Cyclopentylmethyl methanesulfonate

Participants

Reaction Steps

Methanesulfonyl chloride (25.5 mL) was added dropwise to a solution of cyclopentanemethanol (32.4 mL) and triethylamine (46 mL) in dichloromethane (500 ml) at 0° C. After stirring overnight at room temperature, the mixture was sequentially washed with water, 2% hydrochloric acid, 4% aqueous sodium bicarbonate and water again. Following drying over sodium sulfate, the solvent was removed under vacuum, affording crude cyclopentylmethyl methanesulfonate (ca. 50 g) as a colourless oil. A mixture of this product and sodium iodide in acetone (600 ml) was heated at reflux in the dark for 16 hours. After cooling to room temperature, the reaction mixture was poured into petrol ether/water 2:1 (1.5 L) under stirring. The organic layer was washed twice with water, dried (Na2SO4) and carefully concentrated under reduced pressure (50 mm; temperature of the bath <30° C.). The residue was distilled in vacuo. The title product was obtained as a light yellow oil (39 g), by collecting the fraction boiling at 101-102°/70 mm.

Provenance & Evidence