Methanol → (1-Propylcyclobutyl)methanol

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LiBH4 (524 mg, 24 mmol) and methanol (1 mL) were added to a 0° C. solution of 1-2 (1.935 g, 11.4 mmol) in ether (22 mL). After 1 h at 0° C. and 1.5 h at room temperature, 41 mL 2 M NaOH was slowly added and the resulting mixture was stirred for 1 h. The mixture was then extracted with dichloromethane (3×40 mL) and the combined dichloromethane solution was washed with saturated NH4Cl solution and brine (150 mL each). The organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (dichloromethane) gave 1-3 (1.229 g, 87%).

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