Water → HCID 12176451, compound

HRID 2041475Notes

Reaction equation

HRID 2041475 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-e06efbe6d9694caa946db9798ca306a8
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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