Formylcycloheptane → 5-(Cycloheptyl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone

HRID 1631889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631889
[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:33]=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C1COCC1>[CH:26]1([CH:33]([OH:34])[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)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Komponenten

5

Edukt 3

HCID 77961FormylcycloheptaneHCID 2724682Lithium diisopropylamideHCID 155776462-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone

Produkt 1

HCID 668682975-(Cycloheptyl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enoneAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (0.46 g, 2.0 mmol) in anhydrous THF (20 ml) at −78 C under an N2 atmosphere was added dropwise a solution of lithium diisopropylamide (1.22 ml of a 1.8M solution in THF/heptanes/ethyl benzene, 2.2 mmol). The reaction was stirred at −78 C for 90 minutes and then a solution of cycloheptanecarbaldehyde (316 mg, 2.5 mmol) in anhydrous THF (3 ml) was added dropwise. The reaction was stirred at −78 C for a further 30 minutes and then allowed to warm to room temperature over 30 minutes. The reaction was quenched by addition of H2O (25 ml) and extracted with EtOAc (3×20 ml). The combined organic extracts were washed with brine (15 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure to give a brown oil (628 mg). The crude material was purified by flash chromatography over SiO2 using a 100% isohexane to 100% EtOAc gradient to give the desired product as a colourless oil (101 mg).

Aufarbeitung

  1. stirringThe reaction was stirred at −78 C for a further 30 minutes
  2. customThe reaction was quenched by addition of H2O (25 ml)
  3. extractionextracted with EtOAc (3×20 ml)
  4. washThe combined organic extracts were washed with brine (15 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3b27ac8aa63441cd9e0c0734e0eb4beb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791303B2

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