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

HRID 33972

反応式

HRID 33972 の反応式
[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]

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 948262-(Phenylmethyl)oxirane

生成物 1

HCID 137648321-Azido-3-phenylpropan-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 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).

後処理

  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

出典と根拠

ORDレコード
ord-d26986f78c114fd787c307ae06540219
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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