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Acetic Acid → C29H28ClNO2

HRID 865478
ノート
印刷プレビュー

反応式

HRID 865478 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([OH:33])[CH2:21][CH2:22][C:23]4[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=4C(OC)=O)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:34][Mg+].[Br-].[CH3:37][C:38]([OH:40])=O>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([OH:33])[CH2:21][CH2:22][C:23]4[CH:24]=[CH:29][CH:30]=[CH:31][C:32]=4[C:38]([OH:40])([CH3:37])[CH3:34])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=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 176Acetic AcidHCID 540063032-[3-(S)-[3-(2-(7-Chloro-2-quinolinyl)(E/Z)ethenyl)phenyl]-3-hydroxypropyl]benzoic acid methyl esterHCID 178418689HCID 178418689、化合物

生成物 1

HCID 54563620C29H28ClNO2

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 22635083
Tetrahydrofuran toluene
溶媒

実験手順

To a solution of the hydroxyester of Step 2 (38.68 g, 84.36 mmol) in 600 mL of toluene at 0° C. was added slowly 225 mL of 1.5M MeMgBr in toluene:THF 3:1 and the mixture was stirred at r.t. for 4 h. It was then poured into 2 L cold 12% NH4OAc and 25 mL of AcOH were added. The products were extracted in EtOAc, washed with brine, dried over Na2SO4 and concentrated. Flash chromatography of the residue with EtOAc:toluene 15:85 and 25:75 afforded first the methyl ketone derivative, then the title compound. Yield 24.06 g, 62%.

後処理

  1. additionwere added
  2. extractionThe products were extracted in EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customFlash chromatography of the residue with EtOAc:toluene 15:85 and 25:75 afforded first the methyl ketone derivative

出典と根拠

ORDレコード
ord-29f4a3ddf35c4330983b282c96d0ef52
出典データセット
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05565473

反応ノート

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