Triethylamine → (E)-3-(3-methoxyphenyl)acrylic azide

HRID 1852275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852275
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.C1C=CC(P([N:35]=[N+:36]=[N-:37])(C2C=CC=CC=2)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11]([N:35]=[N+:36]=[N-:37])=[O:13])[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6376683-Methoxycinnamic Acid

Produkt 1

HCID 49782297(E)-3-(3-methoxyphenyl)acrylic azideAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of (E)-3-(3-methoxyphenyl)acrylic acid (20 g, 112 mmol) in benzene (200 ml) was added triethylamine (22.72 g, 224 mmol) followed by DPPA (30.9 g, 112 mmol) at room temperature. The reaction mass was stirred at the same temperature for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with dichloromethane. Combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to get crude compound. The crude compound was purified by conventional column chromatography (Silica gel, 60-120 mesh) using 10% ethyl acetate in pet ether as mobile phase to get the desire compound as white solid (18 g, 79%). 1H NMR (400 MHz, CDCl3): δ ppm 7.73-7.69 (d, J=16 Hz, 1H), 7.33-7.29 (t, J=8 Hz, 1H), 7.26 (s, 1H), 7.14-7.12 (d, J=8 Hz, 1H), 7.05 (s, 1H) 6.98-6.96 (d, J=4 Hz, 1H), 6.43-6.39 (d, J=16 Hz, 1H), 3.86 (s, 3H);

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialCombined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto get crude compound
  8. customThe crude compound was purified by conventional column chromatography (Silica gel, 60-120 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-36774318f9f64c51a111e2354364676a
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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