Ethyl formate → 2-Cyclopentyl-6-hydroxymethylene-3-methoxy-cyclohex-2-enone

HRID 1609802Notes

Reaction equation

HRID 1609802 reaction equation
[H-].[Na+].[CH:3](OCC)=[O:4].[CH:8]1([CH:13]2[C:18]([O:19][CH3:20])=[CH:17][CH2:16][CH2:15][C:14]2=[O:21])[CH2:12][CH2:11][CH2:10][CH2:9]1.P([O-])([O-])(O)=O.[Na+].[Na+]>C1C=CC=CC=1>[CH:8]1([C:13]2[C:14](=[O:21])[C:15](=[CH:3][OH:4])[CH2:16][CH2:17][C:18]=2[O:19][CH3:20])[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 8025Ethyl formateHCID 24203Sodium Phosphate, DibasicHCID 24758Sodium hydrideHCID 222600872-Cyclopentyl-3-methoxycyclohex-3-en-1-one

Product 1

HCID 689026292-Cyclopentyl-6-hydroxymethylene-3-methoxy-cyclohex-2-enoneYield 60%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a suspension of sodium hydride (2.04 g, 60% suspension, 51 mmol) in benzene (100 mL), a mixture of ethyl formate (6.7 g) and 2-cyclopentyl-3-methoxycyclohex-3-en-1-one (2.82 g, 17 mmol) in benzene was added dropwise at 5° C. The reaction mixture was stirred at ice temperature for 1 hour and 18 hours at room temperature. The reaction mixture was cooled in ice bath, and 200 mL of 10% sodium hydrogen phosphate solution was added dropwise. The organic layer was separated, and aqueous layer was extracted with ethyl acetate (2×50 mL). Combined organic extract was washed with brine and dried over anhydrous sodium sulfate. Solvent was removed in vacuo and the resulting product was purified on a column of silica gel (Hex:EtOAc) to give the title compound as a viscous liquid (2 g, 60%).

Workup

  1. additionwas added dropwise at 5° C
  2. temperatureThe reaction mixture was cooled in ice bath
  3. customThe organic layer was separated
  4. extractionaqueous layer was extracted with ethyl acetate (2×50 mL)
  5. extractionCombined organic extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customSolvent was removed in vacuo
  9. customthe resulting product was purified on a column of silica gel (Hex:EtOAc)

Sources & evidence

ORD record
ord-44c0b4ba1e0849c4b826fc5e93a5ff95
Source dataset
uspto-grants-2006_01
Patent number
US06982260B1

Reaction notes

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