Diisopropylamine → 5-(Furan-3-yl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone

HRID 336085Notes

Reaction equation

HRID 336085 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15]1[CH2:19][CH2:18][C:17](=[O:20])[C:16]=1[C:21]1[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=1[CH3:29].[O:30]1[CH:34]=[CH:33][C:32]([CH:35]=[O:36])=[CH:31]1>C1COCC1.CCCCCC>[O:30]1[CH:34]=[CH:33][C:32]([CH:35]([OH:36])[CH:18]2[C:17](=[O:20])[C:16]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])=[C:15]([O:14][CH3:13])[CH2:19]2)=[CH:31]1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 103513-FuraldehydeHCID 155776462-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enoneHCID 178418339Butyllithium

Product 1

HCID 666838815-(Furan-3-yl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enoneYield 80.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (527 μl) in THF (5 ml) under nitrogen at −78° C. is added, dropwise, butyl lithium, 2.5M solution in hexane (1.32 ml) and the reaction allowed to stir at −78° C. for 20 minutes. This solution is then added dropwise to a solution of 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (691 mg) in THF (5 ml) under nitrogen at −78° C. and the resulting solution allowed to stir for a further 30 minutes. A solution of 3-furaldehyde (377 mg) in THF (1 ml) is then added in one portion and the reaction is allowed to warm to room temperature and stirred for a further 30 minutes. The reaction is quenched by the addition of saturated ammonium chloride (50 ml) and extracted with ethyl acetate (50 ml). The organic layer is removed and purified by automated flash chromatography to give 5-(furan-3-yl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (784 mg)

Workup

  1. stirringto stir for a further 30 minutes
  2. temperatureto warm to room temperature
  3. stirringstirred for a further 30 minutes
  4. customThe reaction is quenched by the addition of saturated ammonium chloride (50 ml)
  5. extractionextracted with ethyl acetate (50 ml)
  6. customThe organic layer is removed
  7. custompurified by automated flash chromatography

Sources & evidence

ORD record
ord-b76c3b7772a34e9ab9467ddaf7d0eaa5
Source dataset
uspto-grants-2014_11
Patent number
US08889595B2

Reaction notes

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