Ethyl Acetate → HCID 14770844, Verbindung

HRID 1651574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1651574
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10]2)=[C:4]([F:15])[CH:3]=1.[BH4-].[Na+].[OH-].[Na+].C(OCC)(=O)C>C(O)C.C1COCC1>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]2)=[C:4]([F:15])[CH:3]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 14770833HCID 14770833, Verbindung

Produkt 1

HCID 14770844HCID 14770844, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 15.0 g (54.5 mmol) of 3-(4-bromo-2,5-difluorophenyl) cyclopentanone in 150 ml of absolute ethanol and 10 ml of THF was added 2.5 g (65.4 mmol) of sodium borohydride portionwise. The reaction mixture was stirred for 21/2 hours at room temperature, then poured into a mixture of 250 ml of 1.0 N NaOH and 250 ml of ethyl acetate. The organic phase was washed with water, dried (MgSO4), and concentrated. The crude product was chromatographed over silica gel, eluting with 80:20 CHCl3 :EtOAc, to give 10.8 g (72%) of the desired product as a yellow oil.

Aufarbeitung

  1. washThe organic phase was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was chromatographed over silica gel
  5. washeluting with 80:20 CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-5928a982bb79416ab9f797407590d937
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04929613

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