[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol → 3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehyde

HRID 1923572Notes

Reaction equation

HRID 1923572 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[N:6][CH:7]=1>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH:13]=[O:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 66599256[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol

Product 1

HCID 866472723-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehydeYield 40.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol (2.10 g, 10.1 mmol) in DCM (240 mL) was added manganese(IV) oxide (activated 85%, 20.63 g, 201 mmol) and the reaction mixture was stirred vigorously at room temperature for 3 days. The reaction mixture was filtered through dicalite and then fresh manganese(IV) oxide (activated 85%, 20.63 g, 201 mmol) was added and the reaction mixture stirred vigorously at room temperature for another 4 days. The reaction mixture was filtered through dicalite and evaporated. The combined DCM extracts were then dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) gave the title compound (845 mg, 40%) as a white solid. MS: m/e=207.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through dicalite
  2. stirringthe reaction mixture stirred vigorously at room temperature for another 4 days
  3. filtrationThe reaction mixture was filtered through dicalite
  4. customevaporated
  5. dry with materialThe combined DCM extracts were then dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-35f4a96a3148429d92fbd1f8cf80be56
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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