Hydrochloric Acid → HCID 10858216, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (100 mL, 0.72 mol) was added to a solution of (R)-2-methylbutane-1,4-diol (30 g, 0.29 mol) in DCM (600 mL). The solution was cooled to −20° C., and methanesulfonyl chloride (49 mL, 0.63 mol) was added dropwise over 30 min with vigorous stirring. The resulting mixture was stirred for additional 1 h while the temperature was maintained between −20 and −15° C. The mixture was allowed to warm to 0° C. and then poured into cold 1N HCl solution (100 mL). The organic layer was separated and aqueous phase was extracted with DCM (100 mL). The combined organic extracts were washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting product (75.9 g, quant) was used directly for the next step. 1H NMR (400 MHz, CDCl3): δ 4.41-4.24 (m, 2H), 4.12 (dq, 2H), 3.02 (d, 6H), 2.13 (td, 1H), 1.95 (td, 1H), 1.80-1.65 (m, 1H), 1.07 (d, 3H).

Provenance & Evidence