Hydrochloric Acid → HCID 12739856, compound

HRID 2070562Notes

Reaction equation

HRID 2070562 reaction equation
C(O[C:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]=1)C.[CH2:10]([Mg]Br)[CH2:11][CH:12]=[CH2:13].Cl>O1CCCC1>[CH2:13]([C:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]=1)[CH2:12][CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 897773-Ethoxycyclopent-2-en-1-oneHCID 178418797HCID 178418797, compound

Product 1

HCID 12739856HCID 12739856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-ethoxycyclopent-2-enone (2.37 g) in tetrahydrofuran (30 mL) was added dropwise a 0.5M tetrahydrofuran solution of 3-butenylmagnesium bromide (38.4 mL) under nitrogen atmosphere at −78° C. over 10 minutes, followed by stirring at −78° C. for 3 hours and then at room temperature overnight. Then, after addition of 2N aqueous hydrochloric acid solution, the reaction mixture was stirred for 30 minutes and then extracted with ethyl acetate twice. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel to give 3-(3-butenyl)cyclopent-2-enone (1.1 g).

Workup

  1. customat room temperature
  2. customovernight
  3. stirringthe reaction mixture was stirred for 30 minutes
  4. extractionextracted with ethyl acetate twice
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2fe247b6b8064819af340b05c2d03f6c
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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