Dimethylformamide → Dibenzyl ether

Participants

Reaction Conditions

Reaction Steps

Methyl glycoside alcohol 20 (160 mg, 0.32 mmol) was dissolved in THF (0.32 M, 1.0 mL). Then DMF (0.10 mL) was added as a co-solvent. The solution was cooled to 0° C., and NaH (60% dispersion in mineral oil, 19 mg, 0.48 mmol) was added all at once and stirred for 20 minutes. BnBr (0.060 mL, 0.48 mmol) was then added all at once, followed by the addition of TBAI (10 mg). The reaction was allowed to warm to r.t. and stirred overnight. After diluting with Et2O (20 mL), a saturated solution of NH4Cl (10 mL) was slowly added to quench the reaction. The aqueous layer was extracted with EtOAc (2×10 mL). The organic extracts were combined and dried with MgSO4. After filtration and evaporation of the volatiles under reduced pressure, chromatography (20:1→4:1 hexanes:EtOAc) gave benzyl ether I as a colorless oil (160 mg, 84%).

Provenance & Evidence