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Water → 2-{2-[4-(1,3-Dioxolan-2-yl)-phenyl]-ethenyl}-2-tert.-butyl-oxirane

HRID 652580
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 652580
I[CH3:2].CSC.[CH3:6][C:7]([CH3:24])([CH3:23])[C:8](=[O:22])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[O:21][CH2:20][CH2:19][O:18]2)=[CH:13][CH:12]=1.O>CS(C)=O.O1CCCC1>[O:21]1[CH2:20][CH2:19][O:18][CH:17]1[C:14]1[CH:15]=[CH:16][C:11]([CH:10]=[CH:9][C:8]2([C:7]([CH3:24])([CH3:23])[CH3:6])[CH2:2][O:22]2)=[CH:12][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 6328Methyl iodideHCID 543458391-[4-(1,3-Dioxolan-2-yl)phenyl]-4,4-dimethylpent-1-en-3-one

Produkt 1

HCID 201978292-{2-[4-(1,3-Dioxolan-2-yl)-phenyl]-ethenyl}-2-tert.-butyl-oxiraneAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

8.1 g (0.13 mol) of iodomethane are slowly added dropwise to a solution of 9.9 ml (0.135 mol) of dimethyl sulphide in 75 ml of absolute dimethylsulphoxide and 35 ml of absolute tetrahydrofuran, during which the internal temperature must not rise above 35° C. This suspension is subsequently stirred at room temperature overnight, and 15.7 g (0.14 mol) of potassium tert.-butylate are then added in portions. The mixture is subsequently stirred at room temperature for 30 minutes and cooled to 0° C., and 26 g (0.1 mol) of 4,4-dimethyl-1-[4-(1,3-dioxolan-2-yl)phenyl]-1-penten-3-one are added in portions. The reaction mixture is subsequently stirred at room temperature overnight, water is then added and the mixture is extracted three times with toluene. The combined toluene phases are washed with water and saturated sodium chloride solution, dried over sodium sulphate and concentrated. 25.6 g of crude 2-{2-[4-(1,3-dioxolan-2-yl)-phenyl]-ethenyl} -2-tert.-butyl-oxirane are obtained as an oil, which is further reacted directly. ##STR26##

Aufarbeitung

  1. customrise above 35° C
  2. stirringThe mixture is subsequently stirred at room temperature for 30 minutes
  3. temperaturecooled to 0° C.
  4. stirringThe reaction mixture is subsequently stirred at room temperature overnight
  5. extractionthe mixture is extracted three times with toluene
  6. washThe combined toluene phases are washed with water and saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-037bc437145944319a14c15d75cb8025
Quelldatensatz
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04672134

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