Triethylamine → 4-Ethynylbenzyl methanesulfonate

Participants

Reaction Steps

To a solution of 4-ethynylbenzyl alcohol (5.0 g, 37.8 mmol) in CH2Cl2 (50 mL) and triethylamine (Et3N) (14.4 mL, 104.0 mmol) was added mesyl chloride (8.04 mL, 104.0 mmol) at 0° C. and the reaction was allowed to warm to room temperature. Stirring continued for 2 h under argon during which TLC revealed a quantitative conversion into a higher Rf product. Ice cold water was added into the reaction mixture and extracted with Et2O (200 ml). The organic layer was washed with 1N HCL (70 ml), H2O (100 ml), aqueous NaHCO3 (70 ml), and finally H2O (100 ml); and then dried over Na2SO4. Solvent was evaporated off and dried in vacuo to give 7.0 g of compound 3 as brownish oil which was used without further purification.

Provenance & Evidence