4-Toluenesulfonyl chloride → HCID 86628506, Verbindung

HRID 546678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546678
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[Si:19]([O:36][CH2:37][CH2:38][CH:39]([OH:41])[CH3:40])([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C1C=CN=CC=1)C.ClCCCl>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:41][CH:39]([CH3:40])[CH2:38][CH2:37][O:36][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 115299862-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

Produkt 1

HCID 86628506HCID 86628506, VerbindungAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Triethylamine (4.64 mL), p-toluenesulfonyl chloride (4.66 g) and DMAP (271 mg) were added to a solution of 4-(tert-butyldiphenylsilanyloxy)butan-2-ol (7.3 g; CAS #114079-44-6) in 1,2-dichloroethane (80 mL) at 0° C., and the reaction solution was stirred at 60° C. for three hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure. Ethyl acetate and brine were added to the residue, and the organic layer was separated. The resulting organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 6.4 g of the title compound. The property value of the compound is as follows.

Aufarbeitung

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionEthyl acetate and brine were added to the residue
  5. customthe organic layer was separated
  6. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-08896dc689224e6eb5b4919821b4f28d
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935815B2

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