2,2-Dichloro-3-tert-butyldimethylsilyloxy-cyclobutanone → 3-(((1,1-Dimethylethyl)dimethylsilyl)oxy)cyclobutanone

HRID 1170421Notes

Reaction equation

HRID 1170421 reaction equation
Cl[C:2]1(Cl)[CH:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[CH2:4][C:3]1=[O:14]>CO.[Cl-].[NH4+].[Cu].[Zn]>[Si:7]([O:6][CH:5]1[CH2:2][C:3](=[O:14])[CH2:4]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 1

HCID 687641722,2-Dichloro-3-tert-butyldimethylsilyloxy-cyclobutanone

Product 1

HCID 575158533-(((1,1-Dimethylethyl)dimethylsilyl)oxy)cyclobutanoneYield 38.3%

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 21190736Ammonium chloride methanolSolvent

Procedure

To a solution of 2,2-dichloro-3-tert-butyldimethylsilyloxy-cyclobutanone (see, for example, Journal of Organic Chemistry, 44, 2560 (1979)) (3.20 g, 11.9 mmol) in saturated ammonium chloride methanol (70 mL) was added zinc-copper couple (3.89 g, 59.5 mmol) under nitrogen, and the mixture was stirred at room temperature for 24 hours. The mixture was evaporated, and then thereto was added water and the mixture was extracted with ethyl acetate, washed with saturated ammonium chloride water, and then dried over magnesium sulfate, and filtered. The filtrate was evaporated and purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the titled compound (914 mg, 38%) as a colorless oil.

Workup

  1. customThe mixture was evaporated
  2. additionwas added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated ammonium chloride water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. custompurified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-ed54e336b42a4b6d818ef6d20d29def6
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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