Sodium Iodide → HCID 15284038, compound

HRID 1757449Notes

Reaction equation

HRID 1757449 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]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 193880264-Methoxy-4-(3-methanesulfonyl-trans-prop-1-enyl)tetrahydropyran

Product 1

HCID 15284038HCID 15284038, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. customThe cold bath was removed
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue partitioned between ether and H2O
  4. washThe organic phase was washed twice with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered, through a pad of celite
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ede66db32554691b5bd76ea89c64b36
Source dataset
uspto-grants-1995_08
Patent number
US05446062

Reaction notes

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