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

HRID 20388

反応式

HRID 20388 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c1ab604993c74ab588ef23790460be73
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

関連ノート

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