Aluminium lithium hydride → (4-(Benzofuran-2-ylmethoxy)phenyl)methanol

Participants

Reaction Steps

Compound 93 (400 mg, 1.29 mmol) was dissolved in THF (15 mL) and LiAlH4 (49 mg, 1.29 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-(benzofuran-2-ylmethoxy)phenyl)methanol (220 mg, 67%) as a crude product. This was dissolved in toluene (10 mL). The solution was cooled to 0° C. PBr3 (98 μL, 1.04 mmol) was added dropwise over 15 min. The resulting mixture was stirred at room temperature for 1 h. It was then washed with saturated K2CO3 solution and extracted with EtOAc (3×30 mL). The EtOAc layer was washed with brine and dried (MgSO4). The solvent was evaporated off in-vacuo to obtain 2-((4-(bromomethyl)phenoxy)methyl)benzofuran as a colourless oil, (132 mg). This intermediate was used in the following reaction.

Provenance & Evidence