Sodium Azide → 1-Azido-3-phenylpropan-2-ol

HRID 33972

Reaktionsgleichung

Reaktionsgleichung von HRID 33972
[O:1]1[CH2:10][CH:2]1[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C.O>[N:11]([CH2:10][CH:2]([OH:1])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[N+:12]=[N-:13]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 948262-(Phenylmethyl)oxirane

Produkt 1

HCID 137648321-Azido-3-phenylpropan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To the stirring solution of (2,3-epoxypropyl)benzene (1.0 g, 7.5 mmol) in 4 mL DMF was added a solution of sodium azide (0.97 g, 15 mmol) in 4 mL water. The solution was heated to 90° C. for 1 h. The solvent was removed under reduced pressure. The solid residue was partitioned between ethyl acetate and near saturated sodium chloride. The aqueous layer was washed three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and purified on 10 g of silica eluting with 0 to 50% ethyl acetate/hexanes to give a clear oil. NMR (CDCL3) d (1H, 1.97 ppm), m (2H, 2.73-2.82 ppm), m (1H, 3.22-3.30 ppm), dd (1H, 3.36 ppm), m (1H, 3.92-4.02 ppm), m (3H, 7.13-7.28 ppm), m (2H, 7.28-7.34 ppm).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customThe solid residue was partitioned between ethyl acetate and near saturated sodium chloride
  3. washThe aqueous layer was washed three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. custompurified on 10 g of silica eluting with 0 to 50% ethyl acetate/hexanes
  6. customto give a clear oil

Quellen und Nachweise

ORD-Eintrag
ord-d26986f78c114fd787c307ae06540219
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429594B2

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