Boron trifluoride → 5-Acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuran

HRID 1376989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376989
B(F)(F)F.[C:5]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:12]([OH:19])=[C:11]([CH:20](O)[CH:21]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:10]=1[C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:7])[CH3:6].C(=O)([O-])O.[Na+]>ClCCl>[C:5]([O:8][C:9]1[C:14]([C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:13][C:12]2[O:19][C:21]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:20][C:11]=2[C:10]=1[C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 11070377HCID 11070377, Verbindung

Produkt 1

HCID 111128205-Acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuranAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

BF3 etherate (4.7 ml) was added dropwise to a solution of 4-acetoxy-3,5-di-tert-butyl-2-(2,2-diisoamyl-1-hydroxyethyl)-phenol (17.0 g) in dichloromethane (200 ml) under cooling with ice under a nitrogen atmosphere. After stirring the mixture overnight at room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added. After separating the organic layer, the aqueous layer was subjected to extraction with dichloromethane. The extract was combined with the organic layer, washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off to afford 5-acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuran [15.5 g (yield, 95%)] as a colorless oil.

Aufarbeitung

  1. temperatureunder cooling with ice under a nitrogen atmosphere
  2. customAfter separating the organic layer
  3. extractionthe aqueous layer was subjected to extraction with dichloromethane
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-c8c3e030f38c4f29b531e98b292938f9
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663373

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