Reaction #2023716

Reaction equation

12-carboxyhexacyclo[6.6.1.13,6.110,13.02,7.09,14]heptadecene

3,4-dihydro-2H-pyran

→

12-tetrahydropyranyloxycarbonylhexacyclo[6.6.1.13,6.110,13.02,7.09,14]heptadecene

Yield 72.6%

Solvents

tetrahydrofuran

ethyl ether

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Washsuccessive washing with a 3% aqueous solution of Na2CO3, 3% aqueous solution of sodium chloride, and water
3. 3
   DryingAn organic layer was dried over MgSO4
4. 4
   workup.DISTILLATIONThe ethyl ether and unreacted 3,4-dihydro-2H-pyran were distilled off under reduced pressure by an evaporator

Procedure

Next, 2.1 g of the 12-carboxyhexacyclo[6.6.1.13,6.110,13.02,7.09,14]heptadecene and 1.71 g of 3,4-dihydro-2H-pyran were dissolved in 50 ml of tetrahydrofuran, into which 0.03 g of p-toluenesulfonic acid were added. The resultant mixture was reacted at room temperature for 2 hours. The reaction mixture was diluted with 100 ml of ethyl ether, followed by the successive washing with a 3% aqueous solution of Na2CO3, 3% aqueous solution of sodium chloride, and water. An organic layer was dried over MgSO4. The ethyl ether and unreacted 3,4-dihydro-2H-pyran were distilled off under reduced pressure by an evaporator, whereby 2 g of 12-tetrahydropyranyloxycarbonylhexacyclo[6.6.1.13,6.110,13.02,7.09,14]heptadecene were obtained as a viscous liquid.

Source