Furfuryl Alcohol → 2-{[(Oxiran-2-yl)methoxy]methyl}furan

With reference to the chemical reaction formula 7, epichlorohydrin (23.5 mL, 300 mmol), NaOH aqueous solution (22.0 g, 275 mmol) of 50% and TBABr (0.644 g, 2 mmol) as a catalyst are put into a 100 mL round-bottom flask one after another, and intensely magnetic stirred. 2-furanmethanol (9.81 g, 100 mmol) diluted in THF 30 mL is then slowly added by drops into the flask at a room temperature, and then intensely stirred for two hours at a room temperature. Afterwards the reaction liquid is moved to a separatory funnel, into which are added distilled water and EtOAc 200 ml each to wash an organic layer twice and washed with saturated NaCI aqueous solution. After moisture in the funnel is removed by MgSO4, the residue having been filtered and vacuum evaporated is separated to flash chromatography (hexanes:EtOAc=1:1→1:2) to obtain a furfuryl glycidyl ether (13.3 g, 86.3 mmol, 86% of yield) in the form of transparent oil. The data of 1H and 13C-NMR referring to that is as below.

1. additionis then slowly added by drops into the flask at a room temperature
2. customAfterwards the reaction liquid
3. customis moved to a separatory funnel, into which
4. additionare added
5. distillationdistilled water and EtOAc 200 ml each
6. washto wash an organic layer twice
7. washwashed with saturated NaCI aqueous solution
8. customAfter moisture in the funnel is removed by MgSO4
9. filtrationthe residue having been filtered
10. customvacuum evaporated
11. customis separated to flash chromatography (hexanes:EtOAc=1:1→1:2)

ORD record

ord-0837fa5d901d48699a29f408a6c08432

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09035018B2