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Trifluoroacetic acid → 2,4,6-Tri-tert-butyl-5-hydroxy-2,3-dihydrobenzofuran

HRID 1376961
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1376961
C([SiH](CC)CC)C.[C:8]([C:12]1[O:13][C:14]2[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([OH:25])=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:15]=2[CH:16]=1)([CH3:11])([CH3:10])[CH3:9].FC(F)(F)C(O)=O.[OH-].[Na+]>>[C:8]([CH:12]1[CH2:16][C:15]2[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])=[C:18]([OH:25])[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:20][C:14]=2[O:13]1)([CH3:11])([CH3:9])[CH3:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 118228042,4,6-Tri-tert-butyl-5-hydroxybenzofuran

Produkt 1

HCID 110775842,4,6-Tri-tert-butyl-5-hydroxy-2,3-dihydrobenzofuranAusbeute 76,1 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Triethylsilane (76 ml) was added to 2,4,6-tri-tert-butyl-5-hydroxybenzofuran (24.7 g, 82 mmol) and trifluoroacetic acid (38 ml) was added dropwise to the mixture under ice cooling. The mixture was stirred first at 0° C. for 15 min, then at room temperature for 15 min before it was poured into ice water. The mixture was neutralized with an aqueous solution of 1N sodium hydroxide and subjected to extraction with ethyl acetate. The extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (chloroform) to afford 2,4,6-tri-tert-butyl-5-hydroxy-2,3-dihydrobenzofuran [19.0 g (yield, 76%)].

Aufarbeitung

  1. additionwas added dropwise to the mixture under ice cooling
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-daba4c4b9a664edf99373c4cb996fbea
Quelldatensatz
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05663373

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