Ethyl Acetate → HCID 58083503, compound

HRID 1254003Notes

Reaction equation

HRID 1254003 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]([CH3:12])=[N:4]1)[CH3:2].[B-](F)(F)(F)[F:14].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.CCOC(C)=O>C(#N)C.O>[CH2:1]([N:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([F:14])[C:5]([CH3:12])=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2724933SelectfluorHCID 22167575Methyl 1-ethyl-3-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 58083503HCID 58083503, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a flask, methyl 1-ethyl-3-methylpyrazol-5-ylcarboxylate (1.70 g, 0.010 mol, Ref. CN1626520A) was dissolved in 30 mL of acetonitrile and the selectfluor (1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octanium bis(tetrafluoroborate)) (5.30 g, 0.015 mol) was added in batches. After heating to reflux for 1.5 h, the mixture was diluted with 50 mL of water, and then extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with 150 mL of saturated aqueous sodium bicarbonate solution and 150 mL of saturated brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. Column chromatography (EtOAc:P.E.=1:20 as eluent) gave 0.50 g of the title compound as a yellow oil (yield 26%).

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 1.5 h
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic layer was washed with 150 mL of saturated aqueous sodium bicarbonate solution and 150 mL of saturated brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd600d50b8ce484394e7d2a47020ddeb
Source dataset
uspto-grants-2013_06
Patent number
US08455532B2

Reaction notes

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