Chloromethyl Methyl Ether → HCID 17975839, compound

Participants

Reaction Steps

2-Hydroxymethyl-5-[5-(7-trifluoromethyl-quinolin-4-ylsulfanyl)-pentyloxy]-4H-pyran-4-one EHT 5909 (0.10 g, 0.227 mmol) was charged in a 25 mL three necked round bottom flask equipped with a magnetic stirrer and under a nitrogen atmosphere. THF (6 mL) and NaH (60% dispersion in oil, 10 mg, 0.25 mmol) were added at room temperature. After the reaction mixture was stirred for 5 min, methyl choromethyl ether (18.1 μl, 0.24 mmol, 1.05 eq.) was added via syringe and the reaction mixture was stirred for 2 h 30 at room temperature. The reaction mixture was poured in H2O (60 mL) and extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by chromatography on silica using as eluent MeOH:CH2Cl2=2:98. After evaporation and drying to the vacuum pump a white pale yellow solid EHT 2168 was obtained (74 mg, 67% yield).

Provenance & Evidence