Potassium Carbonate → 3-Benzyl-2-cyclopentenol

HRID 1934321Notes

Reaction equation

HRID 1934321 reaction equation
[CH2:1]([C:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])([O-])=O.[K+].[K+]>CCOCC>[CH2:1]([C:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 118299173-Benzylcyclopent-2-en-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 121097083-Benzyl-2-cyclopentenolYield 95.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of compound 3-benzyl-2-cyclopenten-1-one (3.1 g, 18 mmol) in ether (100 mL) was slowly added to a suspension of lithium aluminum hydride (LAH) (684 mg, 0.87 mol) and ether (100 mL) at 0° C. under N2. The resulting mixture was stirred overnight at ambient temperature and cooled to 0° C. Saturated K2CO3 solution was added to quench the excess LAH, the mixture was filtered through Celite and washed with several portions of ether. The combined organic layers were dried (MgSO4) and concentrated in vacuo to give compound the title compound (3 g, 94%) as a colorless oil. NMR(CDCl3):3.41 (ABq, J=6 Hz, 2H, benzylic protons), 4.80 (bs, 1H, CHOH), 5.22 (bs, 1H, olefinic proton), 7.22 (m, 5H, aromatic protons).

Workup

  1. temperaturecooled to 0° C
  2. customto quench the excess LAH
  3. filtrationthe mixture was filtered through Celite
  4. washwashed with several portions of ether
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15544be88820430e968d7a3092ee7cde
Source dataset
uspto-grants-2002_05
Patent number
US06384031B1

Reaction notes

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