Pyridine → 4-(4-Fluoro-2-nitrophenoxy)cyclohexanol methanesulfonate

HRID 846776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846776
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.N1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClC(Cl)Cl>[CH3:25][S:26]([O:13][CH:10]1[CH2:11][CH2:12][CH:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([F:1])=[CH:3][C:4]=2[N+:16]([O-:18])=[O:17])[CH2:8][CH2:9]1)(=[O:28])=[O:27]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 150969794-(4-Fluoro-2-nitrophenoxy)cyclohexanol

Produkt 1

HCID 150969844-(4-Fluoro-2-nitrophenoxy)cyclohexanol methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred mixture of 18.3 parts of 4-(4-fluoro-2-nitrophenoxy)cyclohexanol, 6.23 parts of pyridine and 135 parts of trichloromethane were added dropwise, during a 10 minutes period, 9 parts of methanesulfonyl chloride. Upon completion, stirring was continued overnight at room temperature. The whole was further stirred and refluxed for 2 hours. The reaction mixture was evaporated and the residue was stirred in water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 1,1'-oxybisethane, yielding 8.5 parts of 4-(4-fluoro-2-nitrophenoxy)cyclohexanol methanesulfonate (ester); mp. 111.7° C. (intermediate 102).

Aufarbeitung

  1. additionwere added dropwise, during a 10 minutes period
  2. stirringThe whole was further stirred
  3. temperaturerefluxed for 2 hours
  4. customThe reaction mixture was evaporated
  5. stirringthe residue was stirred in water
  6. extractionThe product was extracted with trichloromethane
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column-chromatography over silica gel
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. customThe residue was crystallized from 1,1'-oxybisethane

Quellen und Nachweise

ORD-Eintrag
ord-629f1580c8fd424e960b635d790cb488
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137896

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