Sodium Hydroxide → (S)-2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)ethanol

Participants

Reaction Steps

(S)-2-tert-Butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)ethyl pivalate (4G, 1.72 g, 4.56 mmol) was dissolved in MeOH (10 mL) and THF (10 mL). Sodium hydroxide (2 M, 9.13 mL) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The aqueous layer was back-extracted with ethyl acetate and the combined organics were dried (MgSO4), concentrated in vacuo and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give a colorless liquid (1.12 g, 84%). 1H-NMR: 300 MHz, (CD3OD) δ: 8.23 (d, 1H), 7.78 (d, 1H), 7.60 (s, 1H), 7.52 (dd, 2H), 5.69 (m, 1H), 3.83 (dd, 1H), 3.61 (m, 1H), 2.71 (s, 3H), 1.18 (s, 9H).

Provenance & Evidence