Acetic Acid → 4-(2-Trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ol

Participants

Reaction Conditions

Reaction Steps

5.82 g (16.7 mmol) of carbonic acid methyl ester 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-yl ester was dissolved in 100 ml of methanol and cooled down to 5° C.; 3.4 ml=3.30 g (18.4 mmol) of sodium methoxide (5.4 molar in MeOH) was added and the reaction mixture then warmed up to room temperature. After one hour, it was poured into crashed ice, the pH was adjusted to 5-6 with AcOH (1N) and the reaction mixture subsequently extracted twice with MeCl2; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, gradient of n-heptane/MeCl2) to give 4.23 g of 4-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ol as light brown oil.

Provenance & Evidence