Trimethylsilyl iodide → 4-(4Iodo-1-oxobutyl)-alpha,alpha-dimethylphenylacetic acid

HRID 1901537Notes

Reaction equation

HRID 1901537 reaction equation
[CH:1]1([C:4](=[O:17])[C:5]2[CH:10]=[CH:9][C:8]([C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.C[Si]([I:22])(C)C.S(=O)(O)[O-].[Na+]>C(Cl)Cl>[I:22][CH2:3][CH2:2][CH2:1][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)=[O:17]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 98560664-(Cyclopropylcarbonyl)-I+-,I+--dimethylbenzeneacetic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 113143824-(4Iodo-1-oxobutyl)-alpha,alpha-dimethylphenylacetic acidYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10.5 g of 4-(cyclopropyl-oxo-methyl)-α,α-dimethylphenylacetic acid, prepared in accordance with Example 2, in 250 mL of CH2Cl2 was cooled in an ice-MeOH bath and 25 g of trimethylsilyliodide was then added rapidly via pipette. The mixture was stirred in the ice bath for one hour, warmed to ambient temperature, and stirred for one hour. A solution of aqueous sodium bisulfite was then added and the mixture was stirred well. The phases were partitioned and the aqueous layer was extracted with CH2Cl2. The combined organics were washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated in vacuo to afford 12.6 g (77%) of 4-(4-iodo-1-oxobutyl)-α,α-dimethylphenylacetic acid.

Workup

  1. temperaturewas cooled in an ice-MeOH bath
  2. stirringthe mixture was stirred well
  3. customThe phases were partitioned
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined organics were washed with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8944c4c555c47bab9dd9d197a6e8b8b
Source dataset
uspto-grants-1996_11
Patent number
US05578610

Reaction notes

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