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

HRID 33967Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 90 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-11e2e4d548d14e1aa79e6f52edb2a596
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429594B2

Reaction notes

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