Sodium Phosphate, Dibasic → 2-Cyclopentyl-3-methoxy-cyclohex-2-enone

HRID 1609801Notes

Reaction equation

HRID 1609801 reaction equation
[CH:1]1([CH:6]2[C:11]([O:12][CH3:13])=[CH:10][CH2:9][CH2:8][C:7]2=[O:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[O-].[Na+].P([O-])([O-])(O)=O.[Na+].[Na+]>C1COCC1>[CH:1]1([C:6]2[C:7](=[O:14])[CH2:8][CH2:9][CH2:10][C:11]=2[O:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 10942334Sodium MethoxideHCID 222600872-Cyclopentyl-3-methoxycyclohex-3-en-1-one

Product 1

HCID 222600712-Cyclopentyl-3-methoxy-cyclohex-2-enoneYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-cyclopentyl-3-methoxycyclohex-3-en-1-one (4.3 g) in dry THF (120 mL), sodium methoxide (1.1 g) was added in portions at room temperature. After stirring the reaction mixture at room temperature for 1.5 hours, cooled in an ice bath, and neutralized with sodium hydrogen phosphate solution. The organic layer was separated, aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting product was purified on a column of silica gel (Hex:EtOAc) to give the title compound as yellow liquid (2.82 g, 65.5%). 1H NMR (CDCl3): δ 1.25–1.8 (m, 8H, 4×CH2), 1.96 (m, 2H, CH2), 2.36 (t, 2H, CH2), 2.56 (t, 2H, CH2), 3.22 (m, 1H, CH), 3.79 (s, 3H, OCH3).

Workup

  1. temperaturecooled in an ice bath
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted with ethyl acetate (2×50 mL)
  4. extractionThe combined organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe resulting product was purified on a column of silica gel (Hex:EtOAc)

Sources & evidence

ORD record
ord-4942629b17274ee0b690cc5a6590fa3c
Source dataset
uspto-grants-2006_01
Patent number
US06982260B1

Reaction notes

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