Water → 4,6-Di-tert-butyl-2,2-diethyl-5-hydroxy-2,3-dihydrobenzofuran

HRID 1900506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900506
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][C:11]1[C:12]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:13][C:14]2[O:18][C:17]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:16][C:15]=2[C:23]=1[C:24]([CH3:27])([CH3:26])[CH3:25])(=O)C.O.[OH-].[Na+]>O1CCCC1>[C:24]([C:23]1[C:15]2[CH2:16][C:17]([CH2:19][CH3:20])([CH2:21][CH3:22])[O:18][C:14]=2[CH:13]=[C:12]([C:28]([CH3:29])([CH3:31])[CH3:30])[C:11]=1[OH:10])([CH3:25])([CH3:27])[CH3:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 110244525-Acetoxy-4,6-di-tert-butyl-2,2-diethyl-2,3-dihydrobenzofuranHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 110987574,6-Di-tert-butyl-2,2-diethyl-5-hydroxy-2,3-dihydrobenzofuranAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium aluminum hydride (76 mg) was suspended in tetrahydrofuran (5 ml) under a nitrogen atmosphere. A solution of 5-acetoxy-4,6-di-tert-butyl-2,2-diethyl-2,3-dihydrobenzofuran (0.17 g, 0.5 mmol) in tetrahydrofuran (5 ml) was added dropwise to the suspension. After heating under reflux for 3 h, the reaction mixture was cooled to room temperature and water was added dropwise. After addition of 1N aqueous sodium hydroxide (5 ml), the mixture was subjected to extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4,6-di-tert-butyl-2,2-diethyl-5-hydroxy-2,3-dihydrobenzofuran [130 mg (yield, 87%)] as a pale yellow oil. Mass 304(M+), 289, 163, 57

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureunder reflux for 3 h
  3. extractionthe mixture was subjected to extraction with diethyl ether
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4b21c77105324461ab3f27a8b47b9122
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05574178

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