Methanol → 2-(3,3-Dimethoxycyclopentyl)ethanol

Participants

Reaction Steps

J. Org. Chem., 1986, 51 (21), 4000-4005. A 5000 mL large neck round bottom flask was charged with a solution of methyl 2-(3,3-dimethoxycyclopentyl)acetate (238 g, 1177 mmol) in THF (1100 mL). To the solution was added LiBH4, 2.0 M in THF (706 mL, 1412 mmol) over approximately 1 min, followed by dropwise addition of methanol (57.1 mL, 1412 mmol). Note: vigorous exotherm. The reaction was stirred for 16 hrs, monitoring by 1H and 13C NMR. The reaction was quenched by the addition of sat'd ammonium chloride solution (600 mL), then diluted with Et2O (˜500 mL), and the layers were separated. The aqueous layer was extracted with CH2Cl2 (300 mL), and the combined organic extracts were concentrated. The resulting oil was diluted with CH2Cl2 (200 mL), dried (MgSO4), filtered and concentrated to yield 2-(3,3-dimethoxycyclopentyl)ethanol (203.3 g, 1167 mmol, 99% yield).

Provenance & Evidence