[4-Nitro-1-(oxan-2-yl)-1H-pyrazol-3-yl]methanol → 4-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde

HRID 2064635Notes

Reaction equation

HRID 2064635 reaction equation
C(OC(C1C(C=O)=NNC=1)=O)C.[N+:13]([C:16]1[C:17]([CH2:27][OH:28])=[N:18][N:19]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:20]=1)([O-:15])=[O:14]>[O-2].[Mn+4].[O-2].CC(C)=O>[N+:13]([C:16]1[C:17]([CH:27]=[O:28])=[N:18][N:19]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:20]=1)([O-:15])=[O:14]

Participants

5

Reactant 2

HCID 22477717[4-Nitro-1-(oxan-2-yl)-1H-pyrazol-3-yl]methanolHCID 178469924HCID 178469924, compound

Product 1

HCID 224778374-Nitro-1-(oxan-2-yl)-1H-pyrazole-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

By proceeding in a manner similar to Reference Example 6(a) above but (i) using [4-nitro-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-3-yl]-methanol (663 mg, Reference Example 53) and manganese (IV) oxide (2.54 g) with acetone as the solvent, (ii) carrying out the reaction at 65° C. for 2 hours and (iii) subjecting the reaction product to flash silica chromatography eluting with a mixture of pentane and ethyl acetate (70:30, v/v), there was prepared 4-nitro-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-3-carbaldehyde (191 mg) as a pale yellow oil. LC-MS (Method H): RT=2.19 minutes, 248.24 (M+H+Na)+.

Workup

  1. customthe reaction at 65° C. for 2 hours
  2. washeluting with a mixture of pentane and ethyl acetate (70:30, v/v), there
  3. customwas prepared 4-nitro-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-3-carbaldehyde (191 mg) as a pale yellow oil

Sources & evidence

ORD record
ord-b8cfde8e15f24e96a38567072179cc24
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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