Dimethylformamide → (4-((5-Methoxybenzofuran-2-yl)methoxy)phenyl)methanol

Participants

Reaction Steps

Sodium ethoxide (62 mg, 0.90 mmol) was added to DMF (3 mL) at 0° C. Resulting suspension was stirred for 15 min. Ethyl 4-hydroxy benzoate (148 mg, 0.90 mmol) was slowly added and resulting mixture was stirred at this temperature for 0.5 h, then allowed to reach room temperature. To this mixture 26 (180 mg, 0.75 mmol) was added. Resulting reaction mixture was stirred at room temperature for 1 h. DMF was evaporated off in-vacuo to give a crude intermediate (150 mg). This was then dissolved in THF (5 mL) and LiAlH4 (34 mg, 0.90 mmol) was added portionwise, with vigorous stirring. The suspension was stirred at room temperature for 1 h. THF was evaporated off in-vacuo. The crude residue was taken up in EtOAc and washed with water, brine and dried (MgSO4). EtOAc was evaporated off in-vacuo to obtain (4-((5-methoxybenzofuran-2-yl)methoxy)phenyl)methanol (120 mg) as a crude product. This was dissolved in toluene (4 mL). The solution was cooled to 0° C. PBr3 (84 μL, 1.04 mmol) was added dropwise over 5 min. The resulting mixture was stirred at room temperature for 1 h. The solvent was evaporated off in-vacuo to obtain 2-((4-(bromomethyl)phenoxy)methyl)-5-methoxybenzofuran as a colourless oil, (90 mg). This intermediate was used in the following reaction.

Provenance & Evidence