Sodium cyanoborohydride → 3-Phenyl-2-furanmethanamine

HRID 915689

Reaktionsgleichung

Reaktionsgleichung von HRID 915689
[C:1]1([C:7]2[CH:11]=[CH:10][O:9][C:8]=2[CH:12]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH3-]C#[N:16].[Na+]>CO>[C:1]1([C:7]2[CH:11]=[CH:10][O:9][C:8]=2[CH2:12][NH2:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 5003444Sodium cyanoborohydrideHCID 134657043-Phenylfuran-2-carbaldehyde

Produkt 1

HCID 691299233-Phenyl-2-furanmethanamineAusbeute 13,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Stir a solution of 3-phenylfuran-2-carbaldehyde (401 mg, 2.33 mmol) and NH4OAc (1.79 g, 23.30 mmol) in methanol (8 mL) at room temperature under nitrogen. Add NaCNBH3 (102 mg, 1.63 mmol). After stirring at room temperature for 24 hours, concentrate the mixture, dilute with water (2 mL), basify with 1N sodium hydroxide, and extract with diethyl ether (4×10 mL). Dry the combined organic phases (magnesium sulfate), filter and concentrate. Perform flash chromatography on silica gel eluting with 9:1 ethyl acetate/MeOH to afford 37 mg of the title compound as a yellow solid. 1H NMR (CDCl3) δ 7.19-7.41 (m, 6H), 6.49 (d, J=2 Hz, 1H), 3.95(s, 2H), 1.80 (br s, 2H).

Aufarbeitung

  1. concentrationconcentrate the mixture
  2. additiondilute with water (2 mL), basify with 1N sodium hydroxide
  3. extractionextract with diethyl ether (4×10 mL)
  4. dry with materialDry the combined organic phases (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-04b5727dfaa54c1e9c06cb272af8238e
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265246B2

Verknüpfte Notizen

Wird geladen…