Triethylamine → METHYL 3-(HYDROXYMETHYL)-5-NITROBENZOATE

HRID 1531939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531939
Cl[C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:3].[BH4-].[Na+].C(N(CC)CC)C>O1CCOCC1>[OH:3][CH2:2][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 74774Methyl 3-(chlorocarbonyl)-5-nitrobenzoateHCID 4311764Sodium borohydride

Produkt 1

HCID 10703703METHYL 3-(HYDROXYMETHYL)-5-NITROBENZOATE

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A stirred solution of the product from step (i) (46.54 g) and sodium borohydride (13.01 g) in 1,4-dioxane (200 ml) was heated at reflux for 17 hours. The mixture was cooled and treated with triethylamine (27.9 ml), poured onto ice-water and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and evaporated. The product was recrystallised from isohexane. Yield 19.38 g.

Aufarbeitung

  1. temperatureat reflux for 17 hours
  2. temperatureThe mixture was cooled
  3. additionpoured onto ice-water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customevaporated
  7. customThe product was recrystallised from isohexane

Quellen und Nachweise

ORD-Eintrag
ord-8ae2dc45fa73405cbbda1d2570d69ebf
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06200981B1

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