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

HRID 1074322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074322
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 (14.3 ml, 160 mmol) was added dropwise to a stirred solution of dimethylsulphoxide (14.3 ml, 200 mmol) in dry dichloromethane (350 ml) at -78° C. After 15 minutes 1-(4-chlorophenyl)-2-cyclopropylethanol (12.98 g, 66 mmol) in dry dichloromethane (120 ml) was added to the mixture. After an hour triethylamine (71.4 ml), 510 mmol) was added and the mixture warmed to room temperature and poured into water. The mixture was extracted with dichloromethane and the combined 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 combined extracts washed with water
  3. customdried
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9adfbe55f66d408eb776c5b3960354f3
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04973767

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