Water → HCID 12176451, compound

HRID 911608Notes

Reaction equation

HRID 911608 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH:5]1([CH2:10][C:11](Cl)=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1.O.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH:5]1([CH2:10][C:11]([C:18]2[CH:19]=[CH:20][C:15]([CH3:21])=[CH:16][CH:17]=2)=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 3485182Cyclopentylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12176451HCID 12176451, compoundYield 91%

Procedure

Add aluminum trichloride (2.719 g, 20.4 mmol) in three portions to a solution of cyclopentylacetyl chloride (2 g, 13.6 mmol) in anhydrous toluene (30 mL) at 0° C. Stir the solution at room temperature overnight. Cool to 0° C., add water and extract the aqueous phase with EtOAc. Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1) to give the desired intermediate as an oil (2.5 g, 91%).

Workup

  1. temperatureCool to 0° C.
  2. extractionextract the aqueous phase with EtOAc
  3. dry with materialDry the organic phase over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1)

Sources & evidence

ORD record
ord-0aebba3508ff4387bb1aa05c2bff5a8f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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