3,4-dihydro-2H-pyran → HCID 118308747, compound

HRID 923500Notes

Reaction equation

HRID 923500 reaction equation
[N+:1]([CH2:4][C:5]1[CH:6]=[N:7][NH:8][CH:9]=1)([O-:3])=[O:2].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.O.CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[N+:1]([CH2:4][C:5]1[CH:6]=[N:7][N:8]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][O:10]2)[CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 90192657HCID 90192657, compound

Product 1

HCID 118308747HCID 118308747, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 430 mg of 4-(nitromethyl)-1H-pyrazole in 4.3 ml of ethyl acetate were added 0.62 ml of 3,4-dihydro-2H-pyran and 129 mg of 4-methylbenzenesulfonic acid monohydrate, followed by stirring at room temperature for 3 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 213 mg of 4-(nitromethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was then evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-581cf09e14d84dd3ba05a9146a9443de
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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