Triethylamine → 4-Methanesulfonyloxyheptane

Participants

Reaction Conditions

Reaction Steps

To an ice cooled solution of 834 mg (7.19 mmol) of 4-heptanol in 35 mL of CH2Cl2 was added 1.5 mL of triethylamine. Next, 0.7 mL (9 mmol) of methanesulfonyl chloride was added, dropwise, over 1 minute. The mixture was stirred at 0° C. for 30 minutes, then extracted with H2O (1×15 mL), 5% NH4OH (2×15 mL), 1M HCl (2×15 mL), and brine (1×15 mL), dried over MgSO4, filtered, and concentrated to an oil. Yield 1.31 g (94%). 1H NMR (300 MHz, CDCl3) d 0.96 (t, 6, J=9), 1.43 (m, 4), 1.64 (m, 4), 3.00 (s, 3), 4.73 (quintet, 1 J=5).

Provenance & Evidence