Dichloromethane → 2-(2-Chloroethoxy)tetrahydro-2H-pyran

Participants

Reaction Conditions

Reaction Steps

1-Chloro ethanol (8.06 g, 100 mmol) was dissolved in dry CH2Cl2 (100 ml ) and cooled to 0° C. in an ice bath under argon. To this stirred solution was added dihydropyran (12.6 g, 150 mmol) followed by pyridinium -p-toluene -4-sulfonate (1.25 g, 5 mmol) and the stirring continued for overnight. The reaction mixture was evaporated to dryness and dissolved in EtOAc (200 ml). The EtOAC extract was washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine (100 ml). The organic extract was dried and evaporated to dryness. The crude material was purified by flash chromatography over silica gel using hexane→CH2Cl2 as the eluent. The pure fractions collected together and evaporated to give 11 g (67%) of pure product.

Provenance & Evidence