Ethanol → 1-Cycloperityl-3-(4-phenoxyphenyl)propane-1,3-dione

HRID 81011

Reaction equation

HRID 81011 reaction equation
[H-].[Na+].[CH:3]1([C:8]([O:10]C)=O)[CH2:7][CH2:6][CH2:5][CH2:4]1.[O:12]([C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)C>C1COCC1>[CH:3]1([C:8](=[O:10])[CH2:26][C:25]([C:22]2[CH:23]=[CH:24][C:19]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:20][CH:21]=2)=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 78365Methyl cyclopentanecarboxylateHCID 2367834'-Phenoxyacetophenone

Product 1

HCID 669269031-Cycloperityl-3-(4-phenoxyphenyl)propane-1,3-dioneYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1.508 g, 37.7 mmol, 60% suspension in mineral oil) was added in small portions to a solution of methyl cyclopentanecarboxylate (1.449 g, 11.31 mmol) and 1-(4-phenoxyphenyl)ethanone (2.00 g, 9.42 mmol) in THF (100 mL). Ethanol (0.5 mL) was then added. The mixture was heated to reflux for 5.5 h, quenched with saturated NaCl (50 mL) and acidified to pH 2 with 1 N HCl. THF was evaporated in vacuo. The residue was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (10 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with 5% ethyl acetate in hexanes and eluting with 5-20% ethyl acetate in hexanes, gave 1-cycloperityl-3-(4-phenoxyphenyl)propane-1,3-dione as white solid (1.837 g, 63% yield). MS (ES+) m/z: 309 (M+H); LC retention time: 5.015 min (analytical HPLC Method A).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5.5 h
  3. customquenched with saturated NaCl (50 mL)
  4. customTHF was evaporated in vacuo
  5. extractionThe residue was extracted with ethyl acetate (3×50 mL)
  6. washThe combined extracts were washed with brine (10 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. washeluting with 5-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-07bdb1babcf84960ac0c28d5d4cad1b1
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Linked notes

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