{5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-methanol → 5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carbaldehyde

HRID 2045947Notes

Reaction equation

HRID 2045947 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:25])([F:24])[F:23])[O:13][N:12]=[C:11]([C:14]3[S:18][C:17]([CH2:19][OH:20])=[C:16]([CH3:21])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1>ClCCl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:23])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[S:18][C:17]([CH:19]=[O:20])=[C:16]([CH3:21])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 1

HCID 66587355{5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-methanol

Product 1

HCID 866812905-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carbaldehydeYield 92.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (12.0 g) is added portion wise to a solution of {5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-methanol (4.63 g) in dichloromethane (80 ml). After 2 hours at room temperature, the reaction mixture is filtered through a plug of Celite and the filtration cake is washed with dichloromethane. The filtrate is concentrated in vacuo to yield 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carbaldehyde (4.25 g) as a yellowish solid. The crude product obtained is used without further purification. MS (HPLC/MS): 408 (MH+). Retention time: 2.16 min.

Workup

  1. filtrationthe reaction mixture is filtered through a plug of Celite
  2. washthe filtration cake is washed with dichloromethane
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-bc3bd6b6aefb4a038d6d1af5ad64a8e1
Source dataset
uspto-grants-2013_11
Patent number
US08592418B2

Reaction notes

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