3-Furanol, tetrahydro- → 3-[(2-Fluorophenyl)methoxy]oxolane

Temperature

50 °C

8.8 g (0.1 mole) of 3-hydroxy-tetrahydrofurane were added dropwise, whilst stirring, to a mixture of 2.8 g (0.12 mole) of sodium hydride (3.5 g of 80% strength sodium hydride in paraffin oil) in 100 ml of absolute dioxan at room temperature. The mixture was then heated for 30 minutes under reflux. After cooling to 50° C., 19 g (0.1 mol) of 2-fluorobenzyl bromide were added dropwise to the sodium salt thus obtained. The mixture was then heated for 3 hours under reflux and was allowed to cool to room temperature, 10 ml of methanol were added to destroy the excess sodium hydride, and the mixture was concentrated by distilling off the solvent in vacuo. The residue was taken up in 100 ml of water and extracted with methylene chloride. The organic phase was dried over sodium sulphate and concentrated. The residue was distilled in vacuo. 15.7 g (80% of theory) of 3-(2-fluorobenzyloxy)-tetrahydrofurane of boiling point 89° C./0.1 mm Hg were obtained.

1. temperatureThe mixture was then heated for 30 minutes
2. temperatureunder reflux
3. customthus obtained
4. temperatureThe mixture was then heated for 3 hours
5. temperatureunder reflux
6. temperatureto cool to room temperature
7. customto destroy the excess sodium hydride
8. concentrationthe mixture was concentrated
9. distillationby distilling off the solvent in vacuo
10. extractionextracted with methylene chloride
11. dry with materialThe organic phase was dried over sodium sulphate
12. concentrationconcentrated
13. distillationThe residue was distilled in vacuo

ORD record

ord-2a65735bcd7b470eb4cf9e43032b2629

Source dataset

uspto-grants-1979_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04146384