Benzyl Bromide → 6-(Benzyloxy)hexahydrofuro[3,2-b]furan-3-ol

Temperature

0 °C

To a solution of sodium hydride (3.24 g, 81.0 mmol) in anhydrous DMF (20 mL) was added hexahydrofuro[3,2-b]furan-3,6-diol (10.1 g, 69.1 mmol) at 0° C. and the mixture was stirred for 1 h at 0° C. To the mixture was added bromomethylbenzene (11.73 g, 68.58 mmol) and the resulting mixture was stirred at rt for 4.5 h, and then quenched with H2O 2O (50 mL). The separated water layer was extracted with EtOAc (250 mL×3). The combined organic layers were washed with H2O (50 mL×6), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1) to give the title compound as light yellow oil (8.1 g, 50%).

1. stirringthe resulting mixture was stirred at rt for 4.5 h
2. customquenched with H2O 2O (50 mL)
3. extractionThe separated water layer was extracted with EtOAc (250 mL×3)
4. washThe combined organic layers were washed with H2O (50 mL×6)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1)

ORD record

ord-9b465cb0c0f44a7a9288d7613edf5cc4

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394281B2