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

Temperature

0 °C

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.

1. customThe reaction mixture was evaporated to dryness
2. dissolutiondissolved in EtOAc (200 ml)
3. extractionThe EtOAC extract
4. washwas washed with 5% NaHCO3 solution (100 ml), water (100 ml) and brine (100 ml)
5. extractionThe organic extract
6. customwas dried
7. customevaporated to dryness
8. customThe crude material was purified by flash chromatography over silica gel
9. customThe pure fractions collected together
10. customevaporated

ORD record

ord-ad1644eb1f104cd6a32f8b4051dbdb59

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05969135