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

HRID 133679

반응식

HRID 133679 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-62cf5075293149dead4f83a36e5a20de
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390906B2

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