Methanol → 3-(2-Acetylphenyl)-1(R)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)propanol

HRID 249042ノート

反応式

HRID 249042 の反応式
C[Mg+].[Br-].[C:4]1(C)C=CC=CC=1.C1COCC1.[Cl:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][C:23]([CH:27]=[CH:28][C:29]3[CH:30]=[C:31]([C@H:35]([OH:48])[CH2:36][CH2:37][C:38]4[CH:47]=[CH:46][CH:45]=[CH:44][C:39]=4[C:40]([O:42]C)=O)[CH:32]=[CH:33][CH:34]=3)=[N:24]2)=[CH:19][CH:18]=1.CO>C1COCC1.O>[C:40]([C:39]1[CH:44]=[CH:45][CH:46]=[CH:47][C:38]=1[CH2:37][CH2:36][C@H:35]([C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([CH:28]=[CH:27][C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[CH:26][C:17]([Cl:16])=[CH:18][CH:19]=3)[N:24]=2)[CH:30]=1)[OH:48])(=[O:42])[CH3:4]

参加物

7

反応物 4

HCID 887MethanolHCID 22635083Tetrahydrofuran tolueneHCID 54006302Methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3(R)-hydroxypropyl)benzoateHCID 178418689HCID 178418689、化合物

生成物 1

HCID 541389713-(2-Acetylphenyl)-1(R)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)propanol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

At 0° C., a 1.5M MeMgBr solution in toluene:THF 1:1 (130 mL, 195 mmol) was added dropwise to a solution of the hydroxyester of Step 3 (11.04 g, 24.1 mmol) (dried in EtOAc and stripped with toluene to remove the H2O) and MeOH (2.0 mL, 49.4 mmol) in 240 mL of anhydrous THF. The reaction mixture was stirred at r.t. for 2.5 h and was then poured into ice cold 25% NH4OAc. The product was extracted into EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:toluene 10:90 and 15:85. [α]D : +23.8° (c=1.04, CHCl3).

後処理

  1. dry with materialdried in EtOAc
  2. extractionThe product was extracted into EtOAc
  3. dry with materialdried over Na2SO4
  4. custompurified by flash chromatography on silica with EtOAc:toluene 10:90 and 15:85
  5. custom+23.8° (c=1.04, CHCl3)

出典と根拠

ORDレコード
ord-bb244d466d1d4fe38f0e0028a18486db
出典データセット
uspto-grants-1993_05
特許番号
US05212180

反応ノート

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