HCID 58497981, compound → HCID 58497942, compound

HRID 1505278Notes

Reaction equation

HRID 1505278 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=[C:11]([CH2:14][OH:15])[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:16]([F:18])([F:17])[F:19])[O:13][N:12]=[C:11]([CH:14]=[O:15])[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 1

HCID 58497981HCID 58497981, compound

Product 1

HCID 58497942HCID 58497942, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

Manganese dioxide (17.7 g, 203 mmol) was added to a solution of [5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-methanol (7.98 g, 25.4 mmol) in chloroform (170 ml). After stirring for 4 h at 60° C. the reaction mixture was cooled to 20° C. and filtered. The filtrate was concentrated and the residue was purified by chromatography over silica (cyclohexane/ethylacetate; 3/1) to give 4.1 g of a yellow oil. 1H-NMR (CDCl3, 400 MHz): 9.93 (s, 1H) 7.42-7.48 (m, 3H), 3.88 (d, 2H), 3.50 (d, 1H).

Workup

  1. temperaturewas cooled to 20° C.
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by chromatography over silica (cyclohexane/ethylacetate; 3/1)

Sources & evidence

ORD record
ord-edb4034edd0542c593c8170ee65927f2
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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