Sodium hydride → 6-(2-(Benzyloxy)ethoxy)hexahydrofuro[3,2-b]furan-3-ol

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Reaction Steps

To a suspension of hexahydrofuro[3,2-b]furan-3,6-diol (7.50 g, 51.37 mmol) in anhydrous DMF (100 mL) was added sodium hydride (60% mineral oil suspension, 2.90 g, 72.39 mmol) at 0° C. in portions under the nitrogen atmosphere. Then the mixture was moved to room temperature and stirred for 15 min. To the mixture was added 2-bromoethoxymethylbenzene (12.26 g, 56.97 mmol), and then the mixture was stirred at 115° C. overnight. The mixture was quenched with water (100 mL), and extracted with DCM (300 mL×3). The combined organic phases were washed with brine (200 mLx3), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica chromatography (EtOAc/PE (v/v)=1/2) to give the title compound as brown liquid (3.90 g, 27%).

Provenance & Evidence