Water → 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde

HRID 1880359Notes

Reaction equation

HRID 1880359 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:6]=1.[Li]CCCC.CN([CH:21]=[O:22])C.O>C1COCC1>[O:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[N:5]1[CH:6]=[C:2]([CH:21]=[O:22])[CH:3]=[N:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 467394664-bromo-1-(oxan-2-yl)-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 838146321-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehydeYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (61 g, 0.264 mol) was dissolved in THF (400 mL). Then 1.6 M n-BuLi (181 mL) was added to the solution which was at −95° C. The reaction mixture was stirred over a period of 45 minutes at the same temperature. Then DMF (22.4 mL, 0.29 mol) was added (the same temperature was maintained). The mixture was allowed to heat up to room temperature before addition of water (100 mL). The organic layer was separated, and the aqueous phase was extracted with ether (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated. The residue was purified by chromatography (EtOAc/hexane, 1:4) to afford 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde (29 g, 57%).

Workup

  1. customwas at −95° C
  2. temperaturewas maintained)
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with ether (3×50 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (EtOAc/hexane, 1:4)

Sources & evidence

ORD record
ord-7f02db3c540b4749ab2a7ed20bc42fef
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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