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

HRID 241522노트

반응식

HRID 241522 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b006be621dcb493eb9cc2ff551efa40c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653000B2

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