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

HRID 1022851Notes

Reaction equation

HRID 1022851 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]

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 866315523-[3-Chloro-4-(hydroxymethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazoleYield 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-f85c306ba61b4cc78dcfd86615aad947
Source dataset
uspto-grants-2014_05
Patent number
US08722673B2

Reaction notes

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