Thioanisole → 2-[(heptylsulfanyl)methyl]-3-methylquinolin-4(1H)-one

HRID 384489ノート

反応式

HRID 384489 の反応式
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:10]=1[CH3:28])C1C=CC=CC=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:21]([S:20][CH2:19][C:11]1[NH:12][C:13]2[C:18]([C:9](=[O:8])[C:10]=1[CH3:28])=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

参加物

4

反応物 2

HCID 7520ThioanisoleHCID 595272964-(Benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline

生成物 1

HCID 595272552-[(heptylsulfanyl)methyl]-3-methylquinolin-4(1H)-one収率 95.1%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To a solution of 4-(benzyloxy)-2-[(heptylsulfanyl)methyl]-3-methylquinoline (150 mg) in trifluoroacetic acid (5 mL) was added thioanisole (150 mg), followed by stirring at room temperature for 16 hours. The reaction mixture was added dropwise to an ice-cold aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate (50 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: chloroform/methanol=10/1) to obtain 2-[(heptylsulfanyl)methyl]-3-methylquinolin-4(1H)-one (110 mg).

後処理

  1. extractionfollowed by extraction with ethyl acetate (50 mL)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

出典と根拠

ORDレコード
ord-7d10b21b5f264ec59469e3058e13c6d9
出典データセット
uspto-grants-2013_02
特許番号
US08367702B2

反応ノート

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