3-Tert-butyl-2,2-dichlorocyclobutanone → 3-Tert-butylcyclobutan-1-one

HRID 20389

反応式

HRID 20389 の反応式
[C:1]([CH:5]1[CH2:8][C:7](=[O:9])[C:6]1(Cl)Cl)([CH3:4])([CH3:3])[CH3:2]>[Zn]>[C:1]([CH:5]1[CH2:8][C:7](=[O:9])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

参加物

3

反応物 1

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

生成物 1

HCID 109314423-Tert-butylcyclobutan-1-one収率 56%

試薬・触媒・溶媒 1

HCID 23994Zinc触媒

実験手順

Saturate dry methanol by stirring with excess ammonium chloride under nitrogen for 1.5 h. Add this saturated solution (150 mL) to 3-tert-butyl-2,2-dichlorocyclobutanone (7.5 g, 38.4 mmol) under nitrogen. To the resulting suspension add freshly activated zinc (15.4 g, 236 mmol). Stir for 5 hours, filter and concentrate. Partition the residue between diethyl ether and water. Discard the aqueous phase and wash the diethyl ether layer with water (twice), 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 desired compound as a clear liquid (2.71 g, 56%).

後処理

  1. concentrationSaturate dry methanol
  2. stirringStir for 5 hours
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPartition the residue between diethyl ether and water
  6. washwash the diethyl ether layer with water (twice), saturated aqueous sodium chloride solution
  7. dry with materialdry (magnesium sulfate)
  8. filtrationfilter
  9. concentrationconcentrate
  10. custompurify
  11. wash(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-a6dce099fbed46a0902d4501d37ea4dd
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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