Ethyl Acetate → [1-(2,5-Dichlorophenyl)-cyclopentyl]-methanol

HRID 2169245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169245
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1([CH:14]=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.[BH4-].[Na+].C(OCC)(=O)C>CO.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 867258941-(2,5-Dichloro-phenyl)-cyclopentanecarbaldehyde

Produkt 1

HCID 86725895[1-(2,5-Dichlorophenyl)-cyclopentyl]-methanolAusbeute 90,82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 1-(2,5-dichlorophenyl)-cyclopentanecarbaldehyde (199) (25 g, 103.305 mmol) in methanol (300 mL), was cooled in ice bath, NaBH4 (7.816 g, 206.612 mmol) was added portion-wise and the mixture was stirred for 3 h at room temperature. Silica thin layer chromatography was performed (10% ethyl acetate in hexane, Rf=0.5). After completion of the reaction, it was quenched with saturated NH4Cl solution (100 mL), methanol was removed from the reaction mixture under reduced pressure, the residue was diluted with water and the mixture was extracted with dichloromethane, the combined organic layer was washed with brine, dried, and concentrated. The concentrate was purified using normal silica gel (100-200 mesh) column chromatography using a gradient eluent of 2 to 10% ethyl acetate in hexane to get [1-(2,5-dichlorophenyl)-cyclopentyl]-methanol (200) (23 g, 90.82%) as a colorless liquid.

Aufarbeitung

  1. customAfter completion of the reaction, it
  2. customwas quenched with saturated NH4Cl solution (100 mL), methanol
  3. customwas removed from the reaction mixture under reduced pressure
  4. additionthe residue was diluted with water
  5. extractionthe mixture was extracted with dichloromethane
  6. washthe combined organic layer was washed with brine
  7. customdried
  8. concentrationconcentrated
  9. customThe concentrate was purified

Quellen und Nachweise

ORD-Eintrag
ord-01dae7a96d774f5eba085a75d850b164
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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