1,2-Dibromoethane → 6-Hydroxy-6-methylheptyl 2-tetrahydropyranyl ether

A small portion of a solution of the product from Step I (21.1 g, 0.102 mol) in THF (105 ml) was added, under nitrogen, to magnesium turnings (5.0 g, 0.204 g-atom). The mixture was warmed in an oil bath at 75°-80° and the reaction was started by the addition of 1.5 ml of a 1M solution of 1,2-dibromoethane in THF. The remaining chloroalkane solution was then added during 20 minutes. The resulting mixture was refluxed for 45 minutes, cooled in an ice bath and treated during 15 minutes with a solution of acetone (9.0 ml, 0.123 ml) in THF (95 ml). It was kept at ambient temperature for 16 hours, cooled in an ice bath and treated during 15 minutes with saturated aqueous NH4Cl (115 ml). The resulting mixture was extracted with EtO. The extract was washed with water and brine, dried (MgSO4) and concentrated to give 30.5 g of crude product. Distillation gave 16.77 g of 6-hydroxy-6-methylheptyl 2-tetrahydropyranyl ether, bp 107°-115° (0.07-0.1 mm Hg). The CI mass spectrum had m/z 231 (M+H)+.

1. temperatureThe mixture was warmed in an oil bath at 75°-80°
2. temperatureThe resulting mixture was refluxed for 45 minutes
3. temperaturecooled in an ice bath
4. temperaturecooled in an ice bath
5. extractionThe resulting mixture was extracted with EtO
6. washThe extract was washed with water and brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customto give 30.5 g of crude product
10. distillationDistillation

ORD record

ord-66fcc0a56e4e4e748e1fa8825e29790f

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05405997