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

HRID 241522Notes

Reaction equation

HRID 241522 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b006be621dcb493eb9cc2ff551efa40c
Source dataset
uspto-grants-2014_02
Patent number
US08653000B2

Reaction notes

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