Water → HCID 13602242, compound

HRID 1607358

Reaction equation

HRID 1607358 reaction equation
[CH3:1][C:2]1([CH3:11])[CH:4]([CH:5]=[O:6])[CH:3]1[C:7]([O:9][CH3:10])=[O:8].[Cl:12][C:13]([Cl:19])([Cl:18])[C:14]([F:17])([F:16])[F:15].[C:20](OC(=O)C)(=[O:22])[CH3:21].O>CN(C=O)C.[Zn]>[CH3:1][C:2]1([CH3:11])[CH:4]([CH:5]([O:6][C:20](=[O:22])[CH3:21])[C:13]([Cl:19])([Cl:12])[C:14]([F:17])([F:16])[F:15])[CH:3]1[C:7]([O:9][CH3:10])=[O:8].[CH3:1][C:2]1([CH3:11])[CH:4]([CH:5]([OH:6])[C:13]([Cl:18])([Cl:12])[C:14]([F:17])([F:16])[F:15])[CH:3]1[C:7]([O:9][CH3:10])=[O:8]

Participants

8

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 96351,1,1-Trichloro-2,2,2-trifluoroethaneHCID 3016263Methyl 3-formyl-2,2-dimethylcyclopropanecarboxylate

Product 2

HCID 13602242HCID 13602242, compoundYield 43%HCID 13956728HCID 13956728, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 156 mg (1.00 mmol) of methyl 2,2-dimethyl-3-formylcyclopropanecarboxylate in 1 ml of DMF, 78 mg (1.19 mmol) of zinc powder and 0.177 ml (1.50 mmol) of 1,1,1-trichlorotrifluoroethane were added at 0° C., and the mixture was stirred at 0° C. for 30 minutes and at 50° C. for 10 hours. Then, 0.5 ml of acetic anhydride was added at room temperature, and the mixture was stirred for 10 minutes. After an addition of 2 ml of water, the mixture was extracted with diethyl ether (2 ml×5 times). The extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=2/3) to isolate 122 mg (35%) of methyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate and 133 mg (43%) of methyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. extractionthe mixture was extracted with diethyl ether (2 ml×5 times)
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was purified by thin layer chromatography (silica gel, dichloromethane/hexane=2/3)

Sources & evidence

ORD record
ord-e37e8065015d4d629a5fa30dae587d86
Source dataset
uspto-grants-1989_09
Patent number
US04864052

Linked notes

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