Reaction #56480

Reaction equation

3-hydroxycaprylonitrile

dihydropyran

p-toluenesulfonic acid

→

title compound

Yield 95.0%

1-Amino-3-(tetrahydro-2H-pyran-2-yloxy)octane

Yield 95.0%

Solvents

ether

Conditions

Workup

1. 1
   WashThe resulting solution is washed with 5% aqueous sodium hydroxide (25 ml.) and water (2×25 ml.)
2. 2
   Dryingdried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   OtherEvaporation of the filtrate in vacuo

Procedure

A mixture of 3-hydroxycaprylonitrile (5.2 g., 36.8 millimole), dihydropyran (3.8 g., 45 millimole), and p-toluenesulfonic acid.hydrate (catalytic amount) is stirred at 25° C. for 16 hours, then diluted with ether (100 ml.). The resulting solution is washed with 5% aqueous sodium hydroxide (25 ml.) and water (2×25 ml.), dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo affords the title compound as a pale yellow oil (7.9 g., 95%), pmr (CDCl3) δ0.93 (3H, t), 2.54 (2H, q) and 4.68 (H, m).

Source