N-Methylmorpholine N-oxide monohydrate → HCID 21948859, 화합물

HRID 2182695노트

반응식

HRID 2182695 반응식
[OH2:1].[CH3:2][N+:3]1([O-])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[N+:10]([C:13]1[CH:22]=[CH:21]C=C2[C:14]=1[CH:15]=[CH:16]C(C=C)=N2)([O-:12])=[O:11]>C(O)(C)C.CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:1][CH:8]([N:3]1[C:4]2[C:14](=[C:13]([N+:10]([O-:12])=[O:11])[CH:22]=[CH:21][CH:5]=2)[CH:15]=[CH:16][CH2:2]1)[CH2:7][OH:6]

참가 물질

7

반응물 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 21948811HCID 21948811, 화합물

생성물 1

HCID 21948859HCID 21948859, 화합물

시약·촉매·용매 4

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

336 mg (2.5 mmol) of N-methylmorpholine-N-oxide hydrate and 10.22 ml of osmium tetroxide solution in isopropanol are added at 0° C. to a solution that consists of 3.18 g (15.88 mmol) of 5-nitro-2-vinylquinoline in 140 ml of acetone and 21 ml of water, and the reaction mixture is stirred for 24 hours at room temperature. Then, the solvent is removed in a vacuum, and the residue is taken up in ethyl acetate. The organic phase is washed with water and saturated sodium chloride solution. The aqueous phase is extracted repeatedly with dichloromethane, diethyl ether and ethyl acetate. The combined organic phases are dried on sodium sulfate. After removal of the solvent and purification of silica gel with hexane-ethyl acetate (0-100%) as well as with ethyl acetate-methanol (0-20%), 1.64 g (44% of theory) of the product is obtained.

후처리

  1. customThen, the solvent is removed in a vacuum
  2. washThe organic phase is washed with water and saturated sodium chloride solution
  3. extractionThe aqueous phase is extracted repeatedly with dichloromethane, diethyl ether and ethyl acetate
  4. customThe combined organic phases are dried on sodium sulfate
  5. customAfter removal of the solvent and purification of silica gel with hexane-ethyl acetate (0-100%) as well as with ethyl acetate-methanol (0-20%), 1.64 g (44% of theory) of the product
  6. customis obtained

출처 및 근거

ORD 기록
ord-ce0a04d964694cad9094c952ca23feea
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06897224B2

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