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

HRID 20389

Reaktionsgleichung

Reaktionsgleichung von HRID 20389
[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]

Komponenten

3

Edukt 1

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

Produkt 1

HCID 109314423-Tert-butylcyclobutan-1-oneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a6dce099fbed46a0902d4501d37ea4dd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745438B2

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