Tetrahydrofuran → 4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehyde

HRID 230828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230828
[CH2:1]([C:3]([C:21]1[CH:32]=[CH:31][C:24]([C:25](N(OC)C)=[O:26])=[C:23]([CH3:33])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH2:1]([C:3]([C:21]1[CH:32]=[CH:31][C:24]([CH:25]=[O:26])=[C:23]([CH3:33])[CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([OH:19])[C:15]([CH3:17])([CH3:18])[CH3:16])=[C:8]([CH3:20])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 577634414-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamide

Produkt 1

HCID 577634244-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-benzaldehydeAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a mixture of enantiomer 2 of 4-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-N-methoxy-2,N-dimethyl-benzamide (0.76 g, 1.75 mmol) and THF (20 mL) is added 1M LAH in THF (1.75 mL, 1.75 mmol) with cooling, and the solution stirred for 1 hour. The solution is diluted with Et2O (100 mL) and washed with 1M HCl (50 mL). The aqueous phase is extracted with Et2O (50 mL). The combined organic layers are washed with 1M HCl (50 mL), brine (50 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (0.48 g, 1.21 mmol, 73%).

Aufarbeitung

  1. temperaturewith cooling
  2. washwashed with 1M HCl (50 mL)
  3. extractionThe aqueous phase is extracted with Et2O (50 mL)
  4. washThe combined organic layers are washed with 1M HCl (50 mL), brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-823ed6e125ae48289902158665b2f8ef
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566803B2

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