4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one → HCID 90462327, compound

HRID 2202118Notes

Reaction equation

HRID 2202118 reaction equation
Cl.[CH3:2][CH:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=1)[CH3:4].C[O:15][CH:16](OC)[C:17](=O)[CH:18]=[CH:19]N(C)C>C(O)C>[CH3:4][CH:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17]([CH:16]=[O:15])=[CH:18][CH:19]=[N:13]2)=[CH:8][CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 27821454-(Dimethylamino)-1,1-dimethoxybut-3-en-2-oneHCID 53420788HCID 53420788, compound

Product 1

HCID 90462327HCID 90462327, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [4-(propan-2-yloxy)phenyl]hydrazine hydrochloride (1 g, 4.93 mmol, 1.00 equiv) and (4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamine (1.4 g, 8.08 mmol, 1.64 equiv) in ethanol (20 mL) was refluxed for 3 h. The resulting mixture was cooled to room temperature and concentrated under vacuum. Acetone (10 mL) and 6N hydrochloric acid (10 mL) was added to dissolve the residue and the resulting solution was stirred at room temperature overnight. The reaction was diluted with 100 mL of dichloromethane and then washed with 3×50 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 3.0-7.0% of methanol in dichloromethane to yield 200 mg (18%) of 1-[4-(propan-2-yloxy)phenyl]-1H-pyrazole-5-carbaldehyde as a yellow oil. LCMS (method A, ESI): RT=1.48 min, m/z=230.9 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum
  2. additionAcetone (10 mL) and 6N hydrochloric acid (10 mL) was added
  3. dissolutionto dissolve the residue
  4. additionThe reaction was diluted with 100 mL of dichloromethane
  5. washwashed with 3×50 mL of brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified on a silica gel column
  9. washeluted with 3.0-7.0% of methanol in dichloromethane

Sources & evidence

ORD record
ord-33e2b8af45394a14837929a45685cf6d
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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