Potassium Carbonate → HCID 90404905, compound

Participants

Reaction Conditions

Reaction Steps

K2CO3 (8.2 g, 59.2 mmol) was added to a stirred solution of methyl 3-hydroxybenzoate (11) (3.0 g, 19.72 mmol) sulfonate (10) (5.33 g, 19.72 mmol) in DMF (30 mL) and the reaction mixture was stirred at 90° C. for 16 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (100-200 silica mesh, 30% EtOAc in hexanes) gave methyl 3-((tetrahydro-2H-pyran-4-yl)methoxy)benzoate (12) as a light yellow solid. Yield (4.8 g, 97%); 1H NMR (400 MHz, DMSO-d6) δ 7.53 (d, J=7.6 Hz, 1H), 7.44-7.40 (m, 2H), 7.22 (dd, J=8.4, 2.4 Hz, 1H), 3.88-3.82 (m, 7H), 3.32 (t, J=1.2 Hz, 2H), 2.02-1.96 (m, 1H), 1.69-1.66 (m, 2H), 1.38-1.28 (m, 2H).

Provenance & Evidence