Sodium Iodide → 4-Methoxy-4-(3-iodo-trans-propenyl)tetrahydropyran
Reaction equation
[CH3:1][O:2][C:3]1([CH2:9]/[CH:10]=[CH:11]/S(C)(=O)=O)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[I-:16].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1(/[CH:9]=[CH:10]/[CH2:11][I:16])[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-2-enyl)tetrahydropyran (505 mg, 2.02 mmol), prepared as in step 5 was added sodium iodide (605 mg, 4.03 mmol), and the reaction was stirred for 15 min. The reaction was partitioned between ethyl acetate and brine. The organic layer was washed twice with brine, dried over MgSO4, filtered and concentrated in vacuo to provide 4-methoxy-4-(3-iodo-trans-propenyl)tetrahydropyran (550 mg, 97%) as a dark yellow oil. The iodide was of sufficient purity to use without further purification.