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

HRID 33967

反応式

HRID 33967 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-11e2e4d548d14e1aa79e6f52edb2a596
出典データセット
uspto-grants-2008_09
特許番号
US07429594B2

関連ノート

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