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

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).

1. customThe reaction was quenched by the addition of sat'd ammonium chloride solution (600 mL)
2. additiondiluted with Et2O (˜500 mL)
3. customthe layers were separated
4. extractionThe aqueous layer was extracted with CH2Cl2 (300 mL)
5. concentrationthe combined organic extracts were concentrated
6. additionThe resulting oil was diluted with CH2Cl2 (200 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-d0db85f205bd4f65bd05ff357b485221

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129398B2