Benzyl 2-cyclopentyl-2-hydroxyacetate → Benzyl 2-keto-2-cyclopentylacetate

HRID 516875Notes

Reaction equation

HRID 516875 reaction equation
[CH:1]1([CH:6]([OH:17])[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>ClCCl>[O:17]=[C:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

3

Reactant 1

HCID 54305517Benzyl 2-cyclopentyl-2-hydroxyacetate

Product 1

HCID 18370535Benzyl 2-keto-2-cyclopentylacetateYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A Dess-Martinn reagent (5.8 g, 13.67 mmol) was added to a solution of benzyl 2-cyclopentyl-2-hydroxyacetate (2.0 g, 8.54 mmol) in dichloromethane (30 ml) at room temperature, and the mixture was stirred for 15 hr. The reaction mixture was quenched with 10% sodium thiosulfate and extracted with dichloromethane. The organic layer was washed with saturated sodium bicarbonate and saturated brine and was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5) to give the title compound as a light yellow oil (1.8 g, yield 90%).

Workup

  1. customThe reaction mixture was quenched with 10% sodium thiosulfate
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated sodium bicarbonate and saturated brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-e9c1a1f8c38d46b8a00355351be27eda
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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