4-Nitrobenzenesulfonyl chloride → 3-((tert-Butyldimethylsilyl)oxy)propyl 4-nitrobenzenesulfonate

HRID 1594933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594933
[O:1]([CH2:9][CH2:10][CH2:11][OH:12])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)([O-:24])=[O:23].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:8][C:5]([Si:2]([O:1][CH2:9][CH2:10][CH2:11][O:12][S:31]([C:28]1[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=1)(=[O:32])=[O:33])([CH3:4])[CH3:3])([CH3:6])[CH3:7]

Komponenten

6

Edukt 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

Produkt 1

HCID 570160853-((tert-Butyldimethylsilyl)oxy)propyl 4-nitrobenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-t-butlydimethylsiloxy-1-propanol, prepared by the method of McDougal, et al. JOC, 1986, 51, 3388, which is incorporated herein by reference, (7.6 g, 40 mmol) and diisopropylethylamine (10.4 mL, 60 mmol) in methylene chloride (200 mL) at 0° C. was treated with p-nitrophenylsulfonyl chloride (9.7 g, 44 mmol), stirred for 3 h, poured into saturated NaHCO3 and extracted with diethyl ether. The extracts were washed with brine, dried (Na2SO4), and concentrated. The residue was chromatographed on silica gel with 5% ethyl acetate/hexanes to provide 6.00 g of the title compound.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washThe extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel with 5% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-53453c790f80432898db7b6bac6350f6
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284796B1

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