Methanesulfonyl chloride → HCID 86635257, compound

Participants

Reaction Steps

3-(Ethylthio)-1-butanol (for example, as prepared for Intermediate 27) (247 mg, 1.84 mmol) was dissolved in DCM (10 ml), and the stirred solution was cooled in an external ice-water bath. Methanesulfonyl chloride (commercially available, for example, from Aldrich) (154 μl, 1.99 mmol) was added and stirring was continued under a nitrogen atmosphere for 2.5 h. The reaction mixture was diluted with further DCM (5 ml) and quenched with saturated aqueous sodium hydrogen carbonate. The layers were separated and the aqueous was extracted with further DCM (×2) (hydrophobic frit). The combined organic solutions were concentrated in vacuo to give the title compound as a colourless oil, which later partially solidified (360 mg, 92%): 1H NMR δ (CDCl3) 4.46-4.32 (2H, m), 3.03 (3H, s), 2.98-2.88 (1H, m), 2.57 (2H, q, J=7.5 Hz), 2.03-1.87 (2H, m), 1.35 (3H, d, J=7 Hz), 1.26 (3H, t, J=7 Hz).

Provenance & Evidence