Isopropanol → 3-Methoxy-5-(propan-2-yloxy)aniline

Participants

Reaction Steps

To a solution of 3-amino-5-methoxyphenol (Example 20, step i, 140 mg, 1.0 mmol), triphenylphosphine (390 mg, 1.5 mmol) and propan-2-ol (90 ul, 1.2 mmol) in THF (3 ml) was added portion wise di-tert-butyl diazocarboxylate (345 mg, 1.5 mmol) at room temperature. After stirring for 3 hours the reaction mixture was diluted with ethyl acetate and extracted with a 1N aqueous solution of HCl. The combined aqueous phases were brought to pH=10 with a aqueous solution of 1N NaOH and then extracted with ethyl acetate. The combined organics were filtered through a hydrophobic frit and the solvents were removed under reduced pressure to give 3-isopropoxy-5-methoxyaniline as a light brown oil (169 mg).

Provenance & Evidence