4-Toluenesulfonyl chloride → p-Toluenesulfonic acid [4-(benzyloxy)-3-methylquinolin-2-yl]methyl ester

HRID 384433노트

반응식

HRID 384433 반응식
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N+:12]([O-])=[C:11]([CH3:20])[C:10]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:23].[K+].[K+].[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(#N)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:20][O:35][S:34]([C:31]2[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=2)(=[O:23])=[O:36])[C:10]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 107077894-Benzyloxy-2,3-dimethylquinoline-1-oxide

생성물 1

HCID 59527351p-Toluenesulfonic acid [4-(benzyloxy)-3-methylquinolin-2-yl]methyl ester수율 40.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of 4-benzyloxy-2,3-dimethylquinoline-1-oxide (21.2 g), potassium carbonate (20.9 g), and acetonitrile (400 mL) was added p-toluenesulfonyl chloride (18.8 g), followed by stirring at room temperature for 12 hours. Insolubles were removed by filtration, and the filtrate was concentrated under reduced pressure. Water (500 mL) was added to the residue, followed by twice extractions with ethyl acetate (500 mL). The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1) to obtain p-toluenesulfonic acid [4-(benzyloxy)-3-methylquinolin-2-yl]methyl ester (13.4 g).

후처리

  1. customInsolubles were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater (500 mL) was added to the residue
  4. extractionfollowed by twice extractions with ethyl acetate (500 mL)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-d435d26f9e9448a59196f79a69f7de66
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367702B2

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