Methanol → 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzaldehyde

HRID 241522ノート

反応式

HRID 241522 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[CH2:12][N:11]=2)=[CH:6][C:5]=1[Cl:27].CC(C[AlH]CC(C)C)C.CO>C(Cl)Cl>[Cl:26][C:21]1[CH:20]=[C:19]([C:13]2([C:15]([F:17])([F:18])[F:16])[CH2:12][N:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:3]=[O:2])=[C:5]([Cl:27])[CH:6]=3)[CH2:14]2)[CH:24]=[C:23]([Cl:25])[CH:22]=1

参加物

5

反応物 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 866910494-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzoic acid methyl ester

生成物 1

HCID 866910504-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzaldehyde収率 25.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-chloro-benzoic acid methyl ester (807 mg, 1.79 mmol) in CH2Cl2 (100 mL) was added a solution of DIBAL (1.97 mL, 1 M in CH2Cl2, 1.97 mmol) with a syringe pump at −75° C. The mixture was stirred for 25 min at this temperature, before methanol (1 mL) was added and warmed to room temperature. Saturared aqueous Na/K-tartrate solution was added and the mixture was extracted three times with CH2Cl2. The organic layers were combined, dried over Na2SO4 and concentrated in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (190 mg, 25%).

後処理

  1. additionwas added
  2. extractionthe mixture was extracted three times with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-b006be621dcb493eb9cc2ff551efa40c
出典データセット
uspto-grants-2014_02
特許番号
US08653000B2

反応ノート

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