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

HRID 33972

반응식

HRID 33972 반응식
[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]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 948262-(Phenylmethyl)oxirane

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d26986f78c114fd787c307ae06540219
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429594B2

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