Trichloroacetyl chloride → 3-Tert-butyl-2,2-dichlorocyclobutanone

HRID 20388

반응식

HRID 20388 반응식
[CH3:1][C:2]([CH3:6])([CH3:5])[CH:3]=[CH2:4].COCCOC.[Cl:13][C:14]([Cl:19])(Cl)[C:15](Cl)=[O:16]>C(OCC)C.[Zn]>[C:2]([CH:3]1[CH2:4][C:15](=[O:16])[C:14]1([Cl:19])[Cl:13])([CH3:6])([CH3:5])[CH3:1]

참가 물질

6

반응물 3

HCID 6420Trichloroacetyl chlorideHCID 80711,2-DimethoxyethaneHCID 112103,3-Dimethyl-1-butene

생성물 1

HCID 685641543-Tert-butyl-2,2-dichlorocyclobutanone

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 3283Diethyl Ether용매2회

실험 절차

Suspend 3,3-dimethyl-1-butene (10 mL, 80.8 mmol), ethylene glycol dimethyl ether (11.5 mL, 106 mmol), and freshly activated zinc (13.8 g, 211 mmol) in dry diethyl ether (100 mL) under a nitrogen atmosphere. Add to this suspension a solution of trichloroacetyl chloride (11.5 mL, 103 mmol) in dry diethyl ether (50 mL) dropwise over 20 minutes. Heat to reflux for 24 hours. Cool to room temperature and filter off the residual solid materials. Concentrate the filtrate and triturate the residue with hexanes. Filter the mixture to remove solid materials. Wash the filtrate solution with saturated aqueous sodium bicarbonate solution (3×), saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the pure fractions and concentrate. Isolate the desired compound by vacuum distillation to give a clear liquid (7.59 g, 48%).

후처리

  1. temperatureHeat
  2. temperatureto reflux for 24 hours
  3. filtrationfilter off the residual solid materials
  4. concentrationConcentrate the filtrate
  5. customtriturate the residue with hexanes
  6. filtrationFilter the mixture
  7. customto remove solid materials
  8. washWash the filtrate solution with saturated aqueous sodium bicarbonate solution (3×), saturated aqueous sodium chloride solution
  9. dry with materialdry (magnesium sulfate)
  10. filtrationfilter
  11. concentrationconcentrate
  12. custompurify
  13. wash(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)
  14. customto give the pure fractions
  15. concentrationconcentrate

출처 및 근거

ORD 기록
ord-c1ab604993c74ab588ef23790460be73
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745438B2

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