Pentane → HCID 22568974, Verbindung

HRID 2299452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299452
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20].C([Li])(C)(C)C.CCCCC.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>CCOCC>[C:19]([C:3]1[CH:4]=[C:5]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:12])[CH3:13])[CH:8]([CH3:9])[CH3:10])[CH:17]=[CH:18][C:2]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35])([CH3:22])([CH3:20])[CH3:21]

Komponenten

6

Edukt 4

HCID 8003PentaneHCID 10928Ethyl chloroformateHCID 22568937HCID 22568937, Verbindung2×HCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 22568974HCID 22568974, VerbindungAusbeute 124,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of (4-bromo-3-tert-butyl-phenoxy)-triisopropyl-silane (Intermediate 105, 1.00 g, 2.60 mmols) in 15 mL Et2O cooled to −78° C. was added 3.6 mL of tert-butyllithium, 1.7 M in pentane (395.0 mg, 6.2 mmols). After stirring for 30 minutes ethyl chloroformate (607.6 mg, 5.6 mmols) was added. The resulting solution was warmed to room temperature and quenched by the addition of saturated aqueous NH4Cl. The mixture was extracted with EtOAc and the combined organic layers dried (MgSO4) concentrated under reduced pressure The residue was chromatographed (2-5% EtOAc-hexanes) to give 1.23 g (88%) of the title compound as a colorless oil.

Aufarbeitung

  1. additionwas added
  2. customquenched by the addition of saturated aqueous NH4Cl
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. concentrationconcentrated under reduced pressure The residue
  6. customwas chromatographed (2-5% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2a1594cdcc76479b9ec853e227248336
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495552B2

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