Sodium borohydride → 4-Hydroxymethyl-2-triethylsilylfuran

HRID 273968

Reaktionsgleichung

Reaktionsgleichung von HRID 273968
[BH4-].[Na+].[CH2:3]([Si:5]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:6]1[O:7][CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[CH3:4]>CO>[OH:12][CH2:11][C:9]1[CH:10]=[C:6]([Si:5]([CH2:13][CH3:14])([CH2:15][CH3:16])[CH2:3][CH3:4])[O:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-

Produkt 1

HCID 150370354-Hydroxymethyl-2-triethylsilylfuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (353 mg, 0.93 mmol) was added portionwise to a solution of 2-triethylsilyl-4-furaldehyde (1.64 g, 7.79 mmol) in methanol (10 ml) at 0°. After 1 hour, most of the methanol was evaporated and the residue dissolved in a minimum amount of dilute hydrochloric acid. Extraction (ethyl acetate), drying (magnesium sulfate) and evaporation gave an oil, which was purified by flash chromatography on silica using 20% ethyl ether/hexane. Fractions with Rf of about 0.07 (10% ethyl ether/hexane) gave after evaporation the title alcohol as a colorless oil.

Aufarbeitung

  1. custommost of the methanol was evaporated
  2. dissolutionthe residue dissolved in a minimum amount of dilute hydrochloric acid
  3. extractionExtraction (ethyl acetate)
  4. customdrying
  5. custom(magnesium sulfate) and evaporation
  6. customgave an oil, which
  7. customwas purified by flash chromatography on silica using 20% ethyl ether/hexane
  8. customFractions with Rf of about 0.07 (10% ethyl ether/hexane) gave
  9. customafter evaporation the title alcohol as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-30041682b03c4af08cb5bea47c723131
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387606

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