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

HRID 33972

Reaction equation

HRID 33972 reaction equation
[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]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 948262-(Phenylmethyl)oxirane

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d26986f78c114fd787c307ae06540219
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Linked notes

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