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

HRID 20389

Reaction equation

HRID 20389 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-a6dce099fbed46a0902d4501d37ea4dd
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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