Triethylamine → HCID 57458019, compound

Participants

Reaction Steps

To a slurry of 2,3-bis-(2-hydroxyethyl)-1-methoxybenzene (50.6 g, 0.258 mol, 1 equiv.) and triethylamine (78.3 g, 0.774 mol, 3 equiv.) in DCM (500 mL) at 0° C., add dropwise a solution of methanesulfonyl chloride (65.0 g, 0.567 mol, 2.2 equiv.) in DCM (100 mL) over 45 min. The addition is exothermic and the methanesulfonyl chloride is added at a rate to keep the temperature below 10° C. After the addition is complete, warm the reaction to RT. Wash the solution with water (2×500 mL), and then brine (750 mL). Dry (sodium sulfate) and concentrate to give the title compound as a dark yellow oil (87.4 g, 96.2%), which is used in the next reaction without further purification. An analytical sample is obtained utilizing silica gel chromatography, eluting with 100% diethyl ether.

Provenance & Evidence