Ethylene Oxide → 2-(2-Triisopropylsilanyloxy-naphthalen-1-yl)-ethanol

HRID 1814336

Reaktionsgleichung

Reaktionsgleichung von HRID 1814336
C([Li])CCC.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].[CH2:28]1[O:30][CH2:29]1.B(F)(F)F.CCOCC>CCOCC>[CH:19]([Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:17][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[CH2:28][CH2:29][OH:30])([CH3:21])[CH3:20]

Komponenten

6

Edukt 4

HCID 6354Ethylene OxideHCID 8000Boron trifluoride etherateHCID 22504240(1-Bromo-naphthalen-2-yloxy)-triisopropyl-silaneHCID 178418339Butyllithium2×

Produkt 1

HCID 225040152-(2-Triisopropylsilanyloxy-naphthalen-1-yl)-ethanolAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-Butyllithium (16.4 mL of 1.6 M soln in hexanes, 26.3 mmol) was stirred with Et2O (60 mL) at −78° C. in an argon-purged, round-bottom flask. A solution of (1-bromo-naphthalen-2-yloxy)-triisopropyl-silane (7.10 g, 18.8 mmol) in Et2O (˜5 ml) was added dropwise to the stirring n-BuLi solution. The reaction was stirred at −78° C. for ten minutes and then a solution of ethylene oxide (1.41 mL, 28.2 mmol) and BF3-Et2O (3.81 mL, 31.0 mmol) in Et2O (˜5 ml) was added via syringe. The reaction was stirred at −78° C. for one hour and then at room temperature for two hours. The reaction was carefully quenched with H2O and was extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. The crude product was purified by gradient elution flash chromatography (SiO2, 100% hexanes to 10% EtOAc-hexanes) to give 2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethanol (3.41 g, 9.91 mmol) as a colorless oil in 53% yield. MS (APCI) m/z 343.2 (M−1).

Aufarbeitung

  1. custompurged
  2. stirringThe reaction was stirred at −78° C. for one hour
  3. customThe reaction was carefully quenched with H2O
  4. extractionwas extracted three times with EtOAc
  5. washwashed with brine solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered through celite
  8. concentrationconcentrated
  9. customThe crude product was purified by gradient elution flash chromatography (SiO2, 100% hexanes to 10% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8eb0ad6b3ca048bf9b5a1318cc9004c8
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875765B2

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