Dimethyl Sulfoxide → 1-(1-Fluorocyclopropyl)-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-one

HRID 400632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400632
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1([CH:15]([OH:29])[CH2:16][C:17]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[O:27][CH3:28])([CH3:19])[CH3:18])[CH2:14][CH2:13]1.C(N(CC)CC)C>ClCCl>[F:11][C:12]1([C:15](=[O:29])[CH2:16][C:17]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[O:27][CH3:28])([CH3:19])[CH3:18])[CH2:13][CH2:14]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 600263391-(1-Fluorocyclopropyl)-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-ol

Produkt 1

HCID 600267971-(1-Fluorocyclopropyl)-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-oneAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel4×

Versuchsvorschrift

6 mL of a 2 M solution of oxalyl chloride in dichloromethane was diluted with 5 mL of dichloromethane and cooled on dry ice/acetone bath. To this solution was added dropwise a solution of 1.5 mL of DMSO in 5 mL of dichloromethane. After 10 minutes, a solution of the crude 1-(1-fluorocyclopropyl)-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-ol (0.8 g, 3 mmol) in 4 mL of dichloromethane was added and the mixture was stirred for 15 minutes. 4 mL of triethylamine was added, the cooling bath was removed, and the reaction mixture was allowed to warm to room temperature, quenched with water, and diluted with hexanes. The organic layer was separated, washed with water, dried, filtered, and concentrated in vacuo. The residue was purified by chromatography over silica gel (eluent: hexanes to hexanes-ethyl acetate (10:1), gradient) to give 0.68 g of the title product as an oil which was used without additional purification.

Aufarbeitung

  1. temperaturecooled on dry ice/acetone bath
  2. customthe cooling bath was removed
  3. customquenched with water
  4. additiondiluted with hexanes
  5. customThe organic layer was separated
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by chromatography over silica gel (eluent: hexanes to hexanes-ethyl acetate (10:1), gradient)

Quellen und Nachweise

ORD-Eintrag
ord-21006c67a4b94d3dbeb40a61c5057aea
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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