Potassium Carbonate → 6-Cyclopentyl-6-[2-(3-ethyl-4-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione

HRID 858567Notes

Reaction equation

HRID 858567 reaction equation
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]C(=O)C)=[C:18]([CH2:26][CH3:27])[CH:17]=3)[CH2:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH2:26][CH3:27])[CH:17]=3)[O:7][C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58762607Acetic acid 4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-ethyl-phenyl ester

Product 1

HCID 99739096-Cyclopentyl-6-[2-(3-ethyl-4-hydroxy-phenyl)-ethyl]-dihydro-pyran-2,4-dioneYield 299%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of acetic acid 4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-ethyl-phenyl ester (0.92 g, 2.47 mmol, from Step 3), potassium carbonate (0.68 g, 4.9 mmol) in MeOH (10 mL) was stirred at rt for 1 h. The reaction mixture was partitioned between 1 N HCl and EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated to a yellow oil. The oil was purified by silica gel chromatography (20% to 40% EtOAc in hexanes) to give the title compound (2.44 g, 59%).

Workup

  1. customThe reaction mixture was partitioned between 1 N HCl and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a yellow oil
  5. customThe oil was purified by silica gel chromatography (20% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-42fa3bf498f24c57917b6acacc21d6ad
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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