1-Heptanethiol → 4-(Benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline

HRID 384441

반응식

HRID 384441 반응식
[CH2:1]([SH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:9]([O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([CH2:27]OS(C2C=CC(C)=CC=2)(=O)=O)[C:18]=1[CH3:39])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO.C[O-].[Na+].CO.C1COCC1>[CH2:9]([O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([CH2:27][S:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:18]=1[CH3:39])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

6

반응물 2

HCID 154221-HeptanethiolHCID 59527351p-Toluenesulfonic acid [4-(benzyloxy)-3-methylquinolin-2-yl]methyl ester

생성물 1

HCID 595272964-(Benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline수율 90.2%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 10942334Sodium Methoxide용매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

1-Heptanethiol (250 mg) was dissolved in methanol (5 mL), to which a solution of 28% sodium methoxide in methanol (0.37 mL) was then added, followed by stirring at room temperature for 15 minutes. The reaction mixture was added to a solution of p-toluenesulfonic acid [4-(benzyloxy)-3-methylquinolin-2-yl]methyl ester (464 mg) in methanol-THF (1:1, 10 mL), followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and water (100 mL) was added to the resulting residue, followed by extraction with ethyl acetate (100 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 4-(benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline (380 mg).

후처리

  1. additionwas then added
  2. stirringby stirring at room temperature for 30 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water (100 mL)
  4. additionwas added to the resulting residue
  5. extractionfollowed by extraction with ethyl acetate (100 mL)
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-dad718cd7b364c2096a6aefe1577d3a2
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367702B2

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