Water → 5-Acetoxy-4,6-di-t-butyl-2-iodomethyl-2-methyl-2,3-dihydrobenzofuran

HRID 367295Notes

Reaction equation

HRID 367295 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:7][C:8]2[O:12][C:11]([CH2:14]OS(C)(=O)=O)([CH3:13])[CH2:10][C:9]=2[C:20]=1[C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:3])[CH3:2].[I-:29].[Na+].O>CN(C)C=O>[C:1]([O:4][C:5]1[C:6]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:7][C:8]2[O:12][C:11]([CH2:14][I:29])([CH3:13])[CH2:10][C:9]=2[C:20]=1[C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 154857215-Acetoxy-4,6-di-t-butyl-2-methanesulfonyloxymethyl-2-methyl-2,3-dihydrobenzofuran

Product 1

HCID 154857225-Acetoxy-4,6-di-t-butyl-2-iodomethyl-2-methyl-2,3-dihydrobenzofuranYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of N,N-dimethylformamide was dissolved 0.55 g of 5-acetoxy-4,6-di-t-butyl-2-methanesulfonyloxymethyl-2-methyl-2,3-dihydrobenzofuran and combined with 3.0 g of sodium iodide, and the mixture was heated under reflux for 24 hours. After cooling, water was added and the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography eluting with n-hexane containing 10% ethyl acetate to give 0.4 g of 5-acetoxy-4,6-di-t-butyl-2-iodomethyl-2-methyl-2,3-dihydrobenzofuran (rotamer mixture) as a colorless oil (yield 68%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel column chromatography
  9. washeluting with n-hexane containing 10% ethyl acetate

Sources & evidence

ORD record
ord-b17eddc908a24f5b965a087cadb26e67
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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