HCID 86681293, compound → HCID 86681295, compound

HRID 2045958Notes

Reaction equation

HRID 2045958 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH2:11][C:10]([C:16]3[CH:21]=[C:20]([Cl:22])[C:19]([Cl:23])=[C:18]([Cl:24])[CH:17]=3)([C:12]([F:15])([F:14])[F:13])[O:9][N:8]=2)[O:4][C:3]=1[CH2:25][OH:26]>ClCCl.O=[Mn]=O>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2[CH2:11][C:10]([C:16]3[CH:17]=[C:18]([Cl:24])[C:19]([Cl:23])=[C:20]([Cl:22])[CH:21]=3)([C:12]([F:15])([F:14])[F:13])[O:9][N:8]=2)[O:4][C:3]=1[CH:25]=[O:26]

Participants

4

Reactant 1

HCID 86681293HCID 86681293, compound

Product 1

HCID 86681295HCID 86681295, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

MnO2 (1.75 g) is added portion wise to a solution of {3-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-2-yl}-methanol (1.72 g) in dichloromethane (40 ml). After 16 hours at room temperature, additional MnO2 (4.37 g) is added portion wise and the reaction mixture is stirred at room temperature for a further 3 hours. 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 3-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-2-carbaldehyde (1.28 g) as a light yellow foam. The crude product obtained is used without further purification. MS (HPLC/MS): 426 (MH+). Retention time: 2.21 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-9d495789f6684f81b6d3c1063608b0cd
Source dataset
uspto-grants-2013_11
Patent number
US08592418B2

Reaction notes

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