Hydrochloric Acid → 1-(1,5-Diethyl-1H-pyrazol-3-yl)ethanone

HRID 1825342Notes

Reaction equation

HRID 1825342 reaction equation
CON(C)[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[N:8]([CH2:13][CH3:14])[N:7]=1)=[O:5].[CH3:16][Mg]Br.C(O)C.Cl>O1CCCC1.CCOCC.CCOC(C)=O.O>[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[N:8]([CH2:13][CH3:14])[N:7]=1)(=[O:5])[CH3:16]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 22145427N-Methoxy-N-methyl-1,5-diethylpyrazole-3-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 221454071-(1,5-Diethyl-1H-pyrazol-3-yl)ethanone

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Methoxy-N-methyl-1,5-diethylpyrazole-3-carboxamide (10.1 g) in dry tetrahydrofuran (180 ml) was cooled in an ice-bath and treated with a 3.0M solution of methylmagnesium bromide in ether (20.68 ml) added dropwise over 10 minutes. After stirring for 1 hour the mixture was treated with a mixture of ethanol (5 ml) and 5M aqueous HCl (1 ml). The mixture was then diluted with EtOAc and water. The organic phase was separated and the aqueous phase extracted twice with EtOAc. The combined organic extracts were dried over MgSO4 and evaporated in vacuo to leave an oil which was chromatographed on silica gel, loading in dichloromethane, and eluting with ethyl acetate/hexane mixtures to give, after evaporation of the requisite fractions, the product as an oil (8.08 g). δ(CDCl3) 1.29 (3H, t, J 7 Hz), 1.45 (3H, t, J 7 Hz), 2.55 (3H, s), 2.64 (2H, q, J 7 Hz), 4.14 (2H, q, J 7 Hz,), 6.55 (1H,s) ppm.

Workup

  1. additionadded dropwise over 10 minutes
  2. customThe organic phase was separated
  3. extractionthe aqueous phase extracted twice with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customevaporated in vacuo
  6. customto leave an oil which
  7. customwas chromatographed on silica gel, loading in dichloromethane
  8. washeluting with ethyl acetate/hexane
  9. customto give
  10. customafter evaporation of the requisite fractions

Sources & evidence

ORD record
ord-0dd08b6a6c924cda9af18eb53cdce4cd
Source dataset
uspto-grants-2006_05
Patent number
US07045619B2

Reaction notes

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