Acetic Acid → 1-Butyl-4-(2-nitro-ethyl)-benzene

HRID 640269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 640269
C(O)(=O)C.[CH2:5]([C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=1)[CH2:6][CH2:7][CH3:8].[BH4-].[Na+]>CS(C)=O>[CH2:5]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=1)[CH2:6][CH2:7][CH3:8]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 592551041-butyl-4-((E)-2-nitro-vinyl)-benzene

Produkt 1

HCID 592553861-Butyl-4-(2-nitro-ethyl)-benzeneAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To an acetic acid (5.7 mL) and dimethyl sulfoxide (95 mL) solution of 1-butyl-4-((E)-2-nitro-vinyl)-benzene (5.7 g, 27.8 mmol) described in Manufacturing Example 70-1-1 was added sodium borohydride (1.68 g, 44.5 mmol) at room temperature while cooling appropriately. This mixture was stirred for 3 hours at room temperature. The mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (1.48 g, 26%).

Aufarbeitung

  1. temperaturewhile cooling appropriately
  2. customThe mixture was partitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-b6c442b95b584ccbb129bb8d7134171c
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691882B2

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