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Methanol → 2-Chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]benzaldehyde

HRID 471380
Notes
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Reaction equation

HRID 471380 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])[O:12][N:11]=2)=[CH:6][C:5]=1[Cl:27].[H-].C([Al+]CC(C)C)C(C)C.CO>C(Cl)Cl>[Cl:27][C:5]1[CH:6]=[C:7]([C:10]2[CH2:14][C:13]([C:19]3[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)[CH:8]=[CH:9][C:4]=1[CH:3]=[O:2].[Cl:27][C:5]1[CH:6]=[C:7]([C:10]2[CH2:14][C:13]([C:19]3[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=3)([C:15]([F:17])([F:16])[F:18])[O:12][N:11]=2)[CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 887MethanolHCID 21225700DiisobutylaluminumhydrideHCID 866585252-Chloro-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzoic Acid Methyl Ester2×

Product 2

HCID 866315512-Chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]benzaldehydeYield 66%
HCID 86631552
3-[3-Chloro-4-(hydroxymethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole
Yield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-Chloro-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzoic acid methyl ester (i.e. the product of Step 1, 2.20 g) in CH2Cl2 was added a solution of diisobutyl aluminium hydride (1 M in CH2Cl2 , 10.7 mL) at −78° C. and kept at this temperature for 30 min. MeOH (25 mL) was added carefully and the mixture was allowed to warm to room temp, when aqueous K-Na-tartrate solution was added. The layers were separated and the aqueous phase was extracted with CH2Cl2, combined organic layers were washed with water, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography on silica gel to obtain the title compound (1.35 g, 66%) and 2-Chloro-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzyl alcohol (0.49 g, 24%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2
  3. washwere washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c7ce752b40d6407a8b93400f90f8d24c
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08633134B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes