Acetic Acid → 1-(2-Nitro-ethyl)-4-phenoxymethyl-benzene

HRID 1691158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691158
C(O)(=O)C.[N+:5](/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)([O-:7])=[O:6].[BH4-].[Na+]>CS(C)=O>[N+:5]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)([O-:7])=[O:6]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 592552121-((E)-2-Nitro-vinyl)-4-phenoxymethyl-benzene

Produkt 1

HCID 592554571-(2-Nitro-ethyl)-4-phenoxymethyl-benzeneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To an acetic acid (4.1 mL) and dimethyl sulfoxide (70 mL) solution of 1-((E)-2-nitro-vinyl)-4-phenoxymethyl-benzene (4.1 g, 16.2 mmol) described in Manufacturing Example 86-1-3 was added sodium borohydride (981 mg, 25.9 mmol) at room temperature while cooling appropriately. This mixture was stirred for 1 hour 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) to obtain the title compound (2.11 g, 51%).

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)

Quellen und Nachweise

ORD-Eintrag
ord-c2ca692d1b434f11a8f8256634daa534
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153662B2

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