Sodium Iodide → 4-Methoxy-4-(3-iodo-trans-propenyl)tetrahydropyran
Reaction equation
[CH3:1][O:2][C:3]1(/[CH:9]=[CH:10]/[CH2:11]S(C)(=O)=O)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[Na+].[I-:17]>CC(C)=O>[CH3:1][O:2][C:3]1(/[CH:9]=[CH:10]/[CH2:11][I:17])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 0° C. solution in acetone of 4-methoxy-4-(3-methanesulfonyl-trans-prop-1-enyl)tetrahydropyran (730 mg, 2.92 mmol), prepared as in step 5, was added NaI (5.84 mmol, 875 mg). The cold bath was removed and the reaction mixture was stirred for 2 hours at ambient temperature. The reaction mixture was then concentrated and the residue partitioned between ether and H2O. The organic phase was washed twice with brine, dried over MgSO4, decolorized with activatedcarbon, filtered, through a pad of celite and concentrated in vacuo. The 4-methoxy-4-(3-iodo-trans -prop-1-enyl)tetrahydropyran (800 mg) so obtained was used without further purification.