Ethylene Oxide → 3-Benzenesulfonyl-3-methyl-butan-1-ol

HRID 2212069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2212069
C([Li])CCC.[C:6]1([S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18]1[O:20][CH2:19]1>O1CCCC1>[C:6]1([S:12]([C:15]([CH3:17])([CH3:16])[CH2:19][CH2:18][OH:20])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 6354Ethylene OxideHCID 199476((1-Methylethyl)sulfonyl)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 149069793-Benzenesulfonyl-3-methyl-butan-1-olAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

A solution of n-butyllithium in cyclohexanes (1.8M, 35.1 ml; 63.18 mmol) was added dropwise to a stirred solution of isopropyl phenyl sulphone (9.95 g, 54 mmol) in tetrahydrofuran (100 ml) keeping the temperature of the mixture below −60° C. The mixture was stirred for 30 min. and ethylene oxide was passed through the reaction mixture for 10 min. The mixture was warmed up to −40° C. for 30 min., then quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica gel (i-hexane:ethyl acetate) to give the title compound (12.3 g, 99%).

Aufarbeitung

  1. customthe temperature of the mixture below −60° C
  2. customquenched with sat. aqueous NH4Cl
  3. extractionextracted into ethyl acetate
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (i-hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f8737e092ee344178f600929b7151bbd
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101892B2

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