Borane;tetrahydrofuran → (5-Chloro-4-methoxy-3-methyl benzofuran-2-yl)-methanol

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Reaction Steps

To 0.31 g (1.3 mmol) 5-chloro-4-methoxy-3-methyl-benzofuran-2-carboxylic acid (Example 116, Step 3) in 10 mL of THF under nitrogen was added 1.0M BH3/THF solution (1.8 mL; 1.8 mmol; 1.4 eq). The reaction was stirred overnight and then quenched cautiously with water and extracted twice with ethyl acetate. The combined organic layers were washed with 1N sodium hydroxide and then brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give (5-chloro-4-methoxy-3-methyl benzofuran-2-yl)-methanol as a white crystalline solid (0.29 g; 99% yield).

Provenance & Evidence