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Water → HCID 58079381, Verbindung

HRID 1748906
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1748906
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CS([Cl:28])(=O)=O.O>ClCCl>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][Cl:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10857542Benzenemethanol, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

Produkt 1

HCID 58079381HCID 58079381, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-(tert-Butyldimethylsilyloxy)benzyl alcohol (101) (prepared by the process described in Wu, Y.-C. et al., J. Am. Chem. Soc., 130, 7148-7152 (2008)) (7.94 g, 31.4 mmol) was dissolved in dichloromethane (150 mL), and cooled to 0° C. To this were sequentially added triethylamine (9.10 mL, 66.7 mmol) and methanesulfonyl chloride (3.80 mL, 49.1 mmol) and stirred for 25 hours after warming up to room temperature. To this was added water, and the product was extracted with dichloromethane (×3). The organic layer was sequentially washed with water (×1) and saturated brine (×1), and dried over anhydrous sodium sulfate. After filtration, the mixture was concentrated under reduced pressure and the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=95/1) to give 3-(tert-butyldimethylsilyloxy)benzyl chloride (102) as a colorless oily substance (5.90 g, 23.0 mmol, 73.1%).

Aufarbeitung

  1. temperatureafter warming up to room temperature
  2. extractionthe product was extracted with dichloromethane (×3)
  3. washThe organic layer was sequentially washed with water (×1) and saturated brine (×1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe mixture was concentrated under reduced pressure
  7. customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=95/1)

Quellen und Nachweise

ORD-Eintrag
ord-25df4e0a60ce44a887bcc3763d0c6d28
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09151739B2

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