Sodium borohydride → 1-Fluoro-3-(2-nitro-ethyl)-5-propoxy-benzene

HRID 20438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20438
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH3:13])[CH:7]=[C:6](/[CH:14]=[CH:15]/[N+:16]([O-:18])=[O:17])[CH:5]=1>C(Cl)(Cl)Cl.C(O)(C)C>[F:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH3:13])[CH:7]=[C:6]([CH2:14][CH2:15][N+:16]([O-:18])=[O:17])[CH:5]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 685582311-Fluoro-3-((E)-2-nitro-vinyl)-5-propoxy-benzene

Produkt 1

HCID 685634311-Fluoro-3-(2-nitro-ethyl)-5-propoxy-benzeneAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Add sodium borohydride (1.30 g, 34.46 mmol) to 1-fluoro-3-((E)-2-nitro-vinyl)-5-propoxy-benzene (1.94 g, 8.61 mmol) and silica gel (17 g) in chloroform (86 mL) and isopropanol (25 mL) at room temperature in portions over 5 minutes. Stir at room temperature 2 hours and filter. Concentrate the filtrate and dissolve in ethyl acetate. Wash with water and saturated aqueous sodium chloride, dry over magnesium sulfate, filter and concentrate. Purify on 40 g silica gel eluting with 100:0 to 70:30 hexanes:ethyl acetate to give 1.1 g (56.2%) of the desired compound as an oil.

Aufarbeitung

  1. filtrationfilter
  2. concentrationConcentrate the filtrate
  3. dissolutiondissolve in ethyl acetate
  4. washWash with water and saturated aqueous sodium chloride
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify on 40 g silica gel eluting with 100:0 to 70:30 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8e83b0027be94771977c2a32d98461f9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745438B2

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