Methanol → HCID 86703524, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 2-fluoroadamantane-2-carboxylate (0.90 g, 4.20 mmol) (Zhurnal Organicheskoi Khimii, 1981, 17, 1642) in tetrahydrofuran (40 mL) was added methanol (0.24 mL, 5.90 mmol), followed by the addition of lithium borohydride solution (2.0 M in tetrahydrofuran, 5.3 mL, 10.60 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes, at ambient temperature for 30 minutes and then at reflux for 1 hour. The reaction mixture was cooled to ambient temperature and poured in small portions into a cooled to 0° C. saturated ammonium chloride solution (25 mL) with stirring. The mixture was stirred at ambient temperature for 1 hour and extracted with ethyl acetate (3×70 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford (2-fluoroadamantan-2-yl)methanol (0.69 g, 88%) as colorless solid: MS (ES+) m/z 223.2 (M+39).

Provenance & Evidence