Sodium Iodide → HCID 15284038, compound

HRID 21903Notes

Reaction equation

HRID 21903 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]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 199309484-Methoxy-4-(3-methanesulfonyl-trans-prop-2-enyl)tetrahydropyran

Product 1

HCID 15284038HCID 15284038, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. customThe reaction was partitioned between ethyl acetate and brine
  2. washThe organic layer was washed twice with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4531a2781c9a433398167495ec1ae910
Source dataset
uspto-grants-1995_06
Patent number
US05426111

Reaction notes

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