Sodium Azide → 1-Azido-3-(4-methoxy-phenyl)-propan-2-ol

HRID 33967

Reaktionsgleichung

Reaktionsgleichung von HRID 33967
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][CH:8]2[CH2:10][O:9]2)=[CH:5][CH:4]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C.O>[N:13]([CH2:10][CH:8]([OH:9])[CH2:7][C:6]1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[N+:14]=[N-:15]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 400042-((4-Methoxyphenyl)methyl)oxirane

Produkt 1

HCID 597965141-Azido-3-(4-methoxy-phenyl)-propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirring solution of 2-(4-methoxy-benzyl)-oxirane (2.0 g, 12.2 mmol) in 10 mL DMF was added a solution of sodium azide (0.87 g, 13.4 mmol) in 2 mL water. The solution was heated to 90° C. for 90 min. The solvents were removed under reduced pressure and the resulting solid residue partitioned between ethyl acetate and water. The aqueous phase was washed three times with 10 mL ethyl acetate. The combined organic layers were dried over magnesium sulfate, then purified on 40 g silica eluting with 5-50% ethyl acetate/hexanes to give the product as a clear oil. NMR (CDCl3) d (1H, 1.82 ppm), m (2H, 2.7-2.8 ppm), dd (1H, 3.25 ppm), dd (1H, 3.35 ppm), s (3H, 3.75 ppm), m (1H, 3.9-4.0 ppm), d (2H, 6.85 ppm), d (2H, 7.10 ppm).

Aufarbeitung

  1. customThe solvents were removed under reduced pressure
  2. customthe resulting solid residue partitioned between ethyl acetate and water
  3. washThe aqueous phase was washed three times with 10 mL ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. custompurified on 40 g silica eluting with 5-50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-11e2e4d548d14e1aa79e6f52edb2a596
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429594B2

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