Dimethyl Sulfate → HCID 9889324, compound

Participants

Reaction Steps

To a solution of 7 (3.00 g, 7.08 mmol) and K2CO3 (1.47 g, 10.6 mmol) in 150 mL THF was added dimethylsulfate (1.07 g, 8.49 mmol) and the solution heated at reflux overnight. The solvent was evaporated and the residue partitioned between 50 mL each of CHCl3 and H2O. The organic phase was separated and washed with saturated brine, dried over magnesium sulfate, filtered and evaporated to provide a yellow solid. Recrystallization from CHCl3/EtOH (1:2, 150 mL) afforded pale-yellow needles. Column chromatography of the evaporated mother liquor (100 g silica gel, 2% MeOH/CH2Cl2) afforded an additional 720 mg of desired product (total yield 2.21 g, 71.3%); mp 204° C. (lit.13 mp 191-194° C.); 1H NMR (CDCl3) δ 3.89 (s, 3 H), 3.94 (s, 3 H), 4.01 (s, 3 H), 6.62 (s, 1 H), 6.78 (s, 1 H), 7.01 (d, 2 H, J=9.1 Hz), 7.83 (d, 2 H, J=9.1 Hz); EI-MS in/z 438 (M+, 65), 311 (100). Anal. calcd for C18H15IO5: C, 49.34; H, 3.45. Found: C, 48.58; H, 3.21.

Provenance & Evidence