Sodium hydride → cis-3-Cyclopropylmethoxy-4-hydroxytetrahydrofuran

Temperature

0 °C

To a stirred solution of cis-3,4-dihydroxytetrahydrofuran (5.8 g, 56 mmol) and bromomethylcyclopropane (5.0 g, 37 mmol) in DMF (100 mL) at 0° C. was added sodium hydride (1.6 g of a 60% suspension in mineral oil, 40 mmol) in portions over a period of 2 h. The resulting solution was stirred at 0° C. for 1 h and then at ambient temperature for 18 h. The solution was concentrated in vacuo and partitioned between EtOAc and water. The organic phase was separated, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography using 1:1 EtOAc:hexanes as eluant to give the title compound as a colorless liquid (1.8 g; TLC Rf=0.4, 1:1 EtOAc:hexanes).

1. waitat ambient temperature for 18 h
2. concentrationThe solution was concentrated in vacuo
3. custompartitioned between EtOAc and water
4. customThe organic phase was separated
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash column chromatography

ORD record

ord-44c508df9fe64c78ba2395d73a81330c

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610692B1