Dimethyl Sulfoxide → 2-(3-Methoxyphenyl)cyclopentan-1-one

HRID 377306

Reaktionsgleichung

Reaktionsgleichung von HRID 377306
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][C:12]2=[O:11])[CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27596482-(3-Methoxyphenyl)-cyclopentanol

Produkt 1

HCID 123629382-(3-Methoxyphenyl)cyclopentan-1-oneAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of oxalic chloride (9.0 ml) in methylene chloride (200 ml) was added dimethyl sulfoxide (9.6 ml) at -78° C. After 10 minutes, to the solution was added a solution of 1-hydroxy-2-(3-methoxyphenyl)cyclopentane (13 g) in methylene chloride (20 ml) at the same temperature. After 15 minutes, to the mixture was added triethylamine at -78° C. and the mixture was warmed at 0° C. for 1 hour. The reaction mixture was washed with water and brine and dried over magnesium sulfate. The organic solution was concentrated and the residue was purified by column chromatography on silica gel to give 2-(3-methoxyphenyl)cyclopentanone (8.9 g).

Aufarbeitung

  1. waitAfter 15 minutes
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic solution was concentrated
  5. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-761c8943b06c4d2591ea631b3a32487e
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025375

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