Ethylene Oxide → 2,3-Di(2-hydroxyethyl)furan

To a solution of the above crude 2-(3-furyl)ethanol in 200 ml of diethyl ether, 74.4 ml (119 mmol) of 1.6 M n-butyl lithium in hexane was added dropwise under ice-cooling, followed by stirring at room temperature for 1 hour. This reaction mixture was cooled to -78° C.; oxirane (obtained by adding dropwise a solution of 20.3 g (162 mmol) of 2-bromoethanol in 50 ml of tetrahydrofuran to a solution of 6.49 g (162 mmol) of sodium hydride (60% dispersion in meneral oil) in 50 ml of tetrahydrofuran, at 50° C., and trapping the resulting oxirane gas with a dry ice-acetone bath) was added; and then, 6.65 ml (54.1 mmol) of a boron trifluoride diethyl etherate was added. This reaction mixture was allowed to warm to room temperature, and stirred overnight. After aqueous sodium hydrogen carbonate was added, the reaction mixture was stirred and extracted with diethyl ether 10 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel flush column chromatography (hexane/ethyl acetate=6/1 to 3/1 to 1/1 to ethyl acetate) to yield the desired product.

1. customat 50° C.
2. additionwas added
3. stirringthe reaction mixture was stirred
4. extractionextracted with diethyl ether 10 times
5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customThe resulting crude product was purified by silica gel
8. customflush column chromatography (hexane/ethyl acetate=6/1 to 3/1 to 1/1 to ethyl acetate)

ORD record

ord-e953047e79914633a092eb1b009b7fd6

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998433