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

HRID 33967

반응식

HRID 33967 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-11e2e4d548d14e1aa79e6f52edb2a596
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429594B2

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