Reaction #95288

Reaction equation

4,4-dimethyl-1-octyn-3-ol

dihydropyran

→

4,4-dimethyl-3-tetrahydropyranyloxy-1-octyne

Conditions

Workup

1. 1
   Otherthe mixture is evaporated in vacuo to an oil
2. 2
   OtherThe oil is chromatographed on 600 g
3. 3
   Washof silica gel and the product is eluted with 5% ethyl acetate in benzene yielding a colorless oil

Procedure

To a solution of 23.1 g. (0.150 mole) of 4,4-dimethyl-1-octyn-3-ol (Example 994) in 126 g. of freshly distilled dihydropyran is added 1 drop of phosphorus oxychloride and the solution is maintained at ambient temperature in a tightly stoppered flask for 20 hours. Five drops of triethylamine are then added and the mixture is evaporated in vacuo to an oil. The oil is chromatographed on 600 g. of silica gel and the product is eluted with 5% ethyl acetate in benzene yielding a colorless oil.

Source