Cyclopropanecarboxaldehyde → HCID 66868045, compound

HRID 1631892Notes

Reaction equation

HRID 1631892 reaction equation
[CH3:1][O:2][C:3]1[CH2:7][CH2:6][C:5](=[O:8])[C:4]=1[C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17].C([N-]C(C)C)(C)C.[Li+].[CH:26]1([CH:29]=[O:30])[CH2:28][CH2:27]1>C1COCC1>[CH:26]1([CH:29]([OH:30])[CH:6]2[C:5](=[O:8])[C:4]([C:9]3[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=3[CH3:17])=[C:3]([O:2][CH3:1])[CH2:7]2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 2724682Lithium diisopropylamideHCID 155776462-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone

Product 1

HCID 66868045HCID 66868045, compoundYield 152%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (0.69, 3.0 mmol) in anhydrous THF (10 ml) at −78 C under an N2 atmosphere was added dropwise a solution of lithium diisopropylamide (1.75 ml of a 1.8M solution in THF/heptanes/ethyl benzene, 3.15 mmol). The reaction was stirred at −78 C for 60 minutes and then cyclopropanecarbaldehyde (0.27 ml, 3.6 mmol) was added dropwise. The reaction was stirred at −78 C for a further 30 minutes and then allowed to warm to room temperature over 210 minutes. The reaction was quenched by addition of H2O (50 ml) and extracted with EtOAc (50 ml). The organic phase was washed with H2O (50 ml) and brine (50 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure to give a brown oil (1.37 g). The crude material was purified by flash chromatography over SiO2 using a 100% isohexane to 100% EtOAc gradient to give the desired product (mix of diastereomers) as a colourless oil (622 mg).

Workup

  1. stirringThe reaction was stirred at −78 C for a further 30 minutes
  2. customThe reaction was quenched by addition of H2O (50 ml)
  3. extractionextracted with EtOAc (50 ml)
  4. washThe organic phase was washed with H2O (50 ml) and brine (50 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7aacc5631f8d4800912e3aaa3f5c4428
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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