Methoxy synthesis (via hydroxyl group): 

 

To a 0°C solution of Hydroxyl compound (1.5 g, 4.3 mmol) in THF (50 ml) was added NaH (225 mg, 8.6 mmol) in portions. After addition, the resulting mixture was stirred at 0 0C for 0.5 h. Then CH3I (0.6 g, 8.6 mmol) was added dropwise at 0°C. After addition, the resulting mixture was allowed to warm to room temperature and stirred for 0.5 h. The mixture was concentrated and the residue was purified by column chromatography (petroleum ether/EtOAc = 40:1 to 10:1 ) which gave the title Methoxy compound as a brown oil (1.3 g, 83.3%). 

 

Patent reference: WO2010016005 (Pfizer)

 

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