Dimethyl Sulfoxide → 1-(4-Chlorophenyl)-2-cyclopropylethan-1-one

HRID 1074321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074321
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:23])[CH2:19][CH:20]2[CH2:22][CH2:21]2)=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18](=[O:23])[CH2:19][CH:20]2[CH2:21][CH2:22]2)=[CH:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 190783841-(4-Chlorophenyl)-2-cyclopropylethanol

Produkt 1

HCID 134886181-(4-Chlorophenyl)-2-cyclopropylethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (5.5 ml, 63 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (5.5 ml, 78 mmol) in dry dichloromethane (150 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (5.00 g, 25.4 mmol) in dry dichloromethane (60 ml) was added to the mixture. After an hour triethylamine (27.5 ml, 197 mmol) was added, the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the extracts washed with water, dried and evaporated in vacuo to give crude 1-(4-chlorophenyl)-2-cyclopropylethanone which was used without further purification.

Aufarbeitung

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe extracts washed with water
  3. customdried
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-51b3843b32364f849a6a32c5cfd6121c
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04973767

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