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p-METHYLACETOPHENONE → 1-[4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol

HRID 1788370
ノート
印刷プレビュー

反応式

HRID 1788370 の反応式
[CH3:1][S:2]([C:5]1[CH:23]=[CH:22][C:8]([O:9][CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([CH3:21])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([N-]C(C)C)(C)C.[Li+].[CH3:32][C:33]1[CH:38]=[CH:37][C:36]([C:39](=[O:41])[CH3:40])=[CH:35][CH:34]=1>O1CCCC1.[Cl-].[Na+].O>[CH3:21][C:13]1[CH:12]=[C:11]([CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH2:1][C:39]([C:36]3[CH:37]=[CH:38][C:33]([CH3:32])=[CH:34][CH:35]=3)([OH:41])[CH3:40])(=[O:4])=[O:3])=[CH:23][CH:22]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8500p-METHYLACETOPHENONEHCID 2724682Lithium diisopropylamideHCID 230180214-(4-Methanesulfonylphenoxymethyl)-2-methylquinoline

生成物 1

HCID 230179531-[4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol収率 66%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回
HCID 57417360
Sodium chloride; water
溶媒

実験手順

Under an atmosphere of argon, a solution of 473 mg (1.44 mmol) of 4-(4-methanesulfonylphenoxymethyl)-2-methylquinoline in tetrahydrofuran was cooled to −78° C. and then, 1.44 mL (1.44 mmol) of 2 M lithium diisopropylamide was added thereto and stirred for 40 minutes. Into this solution was dropped a solution of 194 mg (1.59 mmol) of p-methylacetophenone in tetrahydrofuran, followed by stirring for 2.5 hours. The reaction was stopped by the addition of saturated brine, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated under a reduced pressure. The obtained residue was purified by column chromatography on silica gel (developing solvent; hexane:ethyl acetate=1:1 to 1:2) to obtain 440 mg (0.95 mmol) of 1-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol (VIII-57). Its physical property is shown below.

後処理

  1. stirringby stirring for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (developing solvent; hexane:ethyl acetate=1:1 to 1:2)

出典と根拠

ORDレコード
ord-97adc6632ffe4899b931aa4034848e5d
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07511144B2

反応ノート

読み込み中…

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