Methyl iodide → HCID 86758861, compound

HRID 1859414Notes

Reaction equation

HRID 1859414 reaction equation
[CH3:1]I.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C@@H:12]2[C@H:17]3[CH2:18][O:19][C@H:15]([O:16]3)[C@H:14]([O:20][S:21]([C:24]3[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C@H:13]2[OH:31])=[CH:7][CH:6]=1>CN(C)C=O.[Ag]=O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C@@H:12]2[C@H:17]3[CH2:18][O:19][C@H:15]([O:16]3)[C@H:14]([O:20][S:21]([C:24]3[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C@H:13]2[O:31][CH3:1])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 86758862HCID 86758862, compound

Product 1

HCID 86758861HCID 86758861, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (54 ml, 954 mmol) and silver oxide (18.4 g, 79.5 mmol) are added to a solution of compound 88 (3.36 g, 7.95 mmol) in dry N,N-dimethylformamide (8 ml). After stirring for 16 h, the mixture is filtered (Celite), diluted with ethyl acetate (300 ml), washed with water (3×100 ml), dried (sodium sulphate), filtered, concentrated and purified by chromatography on silica to give the derivative 89 (3.23 g, 80%).

Workup

  1. filtrationthe mixture is filtered (Celite)
  2. additiondiluted with ethyl acetate (300 ml)
  3. washwashed with water (3×100 ml)
  4. dry with materialdried (sodium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-6a15ab93db7b40cbabec151f6efb9ac0
Source dataset
uspto-grants-2003_03
Patent number
US06528497B1

Reaction notes

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