StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Diisobutylaluminum hydride → 2,2,6-Trimethyl-heptan-1-ol

HRID 2216687
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2216687
C[O:2][C:3](=O)[C:4]([CH3:12])([CH3:11])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:11][C:4]([CH3:12])([CH2:5][CH2:6][CH2:7][CH:8]([CH3:9])[CH3:10])[CH2:3][OH:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydride2×HCID 216784792,2,6-Trimethyl-heptanoic acid methyl ester

Produkt 1

HCID 219435032,2,6-Trimethyl-heptan-1-olAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2,2,6-Trimethyl-heptanoic acid methyl ester (1.97 g, 10.6 mmol) was taken up in toluene (65 mL) and cooled to −78° C. DiBALH (12.7 mL of a 1 N solution in toluene) was added dropwise. After 45 min, 1.5 mL DiBALH was added. After 2 h, the reaction was quenched by the addition of 15 mL MeOH at −78° C. The mixture was warmed to ambient temperature, and then cooled again to −78° C. for the addition of 10 mL 1 N HCl. The mixture was extracted with EtOAc (3×15 mL). The combined organics were washed with brine, dried (MgSO4), filtered and concentrated. The residual oil was purified via silica gel chromatography (95/5 Hexane/EtOAc) to give 2,2,6-Trimethyl-heptan-1-ol (0.88 g). m/z 159 (M+).

Aufarbeitung

  1. waitAfter 2 h
  2. customthe reaction was quenched by the addition of 15 mL MeOH at −78° C
  3. temperatureThe mixture was warmed to ambient temperature
  4. temperaturecooled again to −78° C. for the addition of 10 mL 1 N HCl
  5. extractionThe mixture was extracted with EtOAc (3×15 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residual oil was purified via silica gel chromatography (95/5 Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-f9b6b8000e054375b355f581269a6d7e
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07112610B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion