Aluminium lithium hydride → [1-(Tetrahydro-pyran-2-yloxy)-cyclopropyl]-methanol

Participants

Reaction Conditions

Reaction Steps

1-(Tetrahydro-pyran-2-yloxy)-cyclopropanecarboxylic acid methyl ester (3.50 g, 17.50 mmol) was dissolved in diethyl ether (85 mL) and a 2.0 M solution of lithium aluminum hydride in diethyl ether (8.75 mL, 17.50 mmol) was added. Upon complete addition, the reaction was refluxed under nitrogen for 1 h. Upon cooling to 25° C., the excess lithium aluminum hydride was hydrolyzed by the addition of ice chips. The organic layer was seated, washed with water (2×20 mL), dried over magnesium sulfate and concentrated in vacuo to afford [1-(tetrahydro-pyran-2-yloxy)-cyclopropyl]-methanol (2.81 g, 93%) as a clear, thick oil: H1-NMR (400 MHz, CDCl3) δ 0.5-1.0 (4H, m), 1.40-2.0 (6H, m), 3.0-3.2 (2H, m), 3.3-4.3 (2H, m), 4.5-4.7 (1H, m), 4.75-5.0 (1H, m).

Provenance & Evidence