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

HRID 384441

反応式

HRID 384441 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 10942334Sodium Methoxide溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dad718cd7b364c2096a6aefe1577d3a2
出典データセット
uspto-grants-2013_02
特許番号
US08367702B2

関連ノート

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