Lithium diisopropylamide → 2-(4-Benzyloxy-2,6-dimethylphenyl)-3-methoxy-5-[1-(tetrahydropyran-4-yl)-methylidene]cyclopent-2-enone

HRID 1193038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193038
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[C:17](=[O:23])[CH2:18][CH2:19][C:20]=2[O:21][CH3:22])=[C:11]([CH3:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[O:33]1[CH2:38][CH2:37][CH:36]([CH:39]=O)[CH2:35][CH2:34]1.CC(C)([O-])C.[K+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[C:17](=[O:23])[C:18](=[CH:39][CH:36]3[CH2:37][CH2:38][O:33][CH2:34][CH2:35]3)[CH2:19][C:20]=2[O:21][CH3:22])=[C:11]([CH3:24])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 2724682Lithium diisopropylamideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 23665647Potassium tert-butoxideHCID 580708252-(4-Benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone

Produkt 1

HCID 667096072-(4-Benzyloxy-2,6-dimethylphenyl)-3-methoxy-5-[1-(tetrahydropyran-4-yl)-methylidene]cyclopent-2-enone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2-(4-benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone (1.93 g, 6.0 mmol) in THF (25 ml) under a nitrogen atmosphere at −78° C. is added a solution of lithium diisopropylamide (3.33 ml, 6.0 mmol, 1.8M in tetrahydrofuran) dropwise over 1 minute. The reaction is then stirred at −78° C. for 30 minutes followed by the addition of 4-tetrahydropyran carbaldehyde (0.684 g, 6.0 mmol) in one portion. After a further 5 minutes at −78° C. the reaction is allowed to warm to ambient temperature and stir for an additional 1 hour. Potassium tert-butoxide (1.10 g, 9.82 mmol) is then added in one portion and the reaction mixture is allowed to stir for a further 1 hour at room temperature. After quenching with saturated ammonium chloride solution (50 ml) the crude product is extracted into ethyl acetate (50 ml), and the organic phase is dried over anhydrous magnesium sulfate and concentrated in vacuo. Purification by flash column chromatography affords 2-(4-benzyloxy-2,6-dimethylphenyl)-3-methoxy-5-[1-(tetrahydropyran-4-yl)-methylidene]cyclopent-2-enone as a white solid.

Aufarbeitung

  1. waitAfter a further 5 minutes at −78° C. the reaction is allowed
  2. temperatureto warm to ambient temperature
  3. stirringstir for an additional 1 hour
  4. stirringto stir for a further 1 hour at room temperature
  5. customAfter quenching with saturated ammonium chloride solution (50 ml) the crude product
  6. extractionis extracted into ethyl acetate (50 ml)
  7. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-152421b166b0419bb7930cdcbb2cb909
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680339B2

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