Ammonium Chloride → HCID 86602516, compound

HRID 30704

Reaction equation

HRID 30704 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][O:12][C:13]([CH2:15]P(=O)(OCC(F)(F)F)OCC(F)(F)F)=[O:14].C1OCCOCCOCCOCCOCCOC1.[F:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]2[N:59]([CH3:60])[N:58]=[CH:57][C:56]=2[CH:61]=O)=[CH:51][CH:50]=1.[Cl-].[NH4+]>O1CCCC1>[F:48][C:49]1[CH:50]=[CH:51][C:52]([C:55]2[N:59]([CH3:60])[N:58]=[CH:57][C:56]=2/[CH:61]=[CH:15]\[C:13]([O:12][CH3:11])=[O:14])=[CH:53][CH:54]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 184894Nsc 634137HCID 3251421Potassium bis(trimethylsilyl)amideHCID 231574845-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 86602516HCID 86602516, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium bis(trimethylsilyl)amide (20% toluene solution, 3.05 g) was added to a mixture of bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate (973 mg), 18-crown-6 (4.04 g) and tetrahydrofuran (50 mL) at −78° C. Furthermore, 5-(4-fluorophenyl)-1-methyl-1H-pyrazole-4-carbaldehyde (312 mg) was added and the mixture was stirred overnight while allowing to warm from −78° C. to room temperature. Saturated aqueous ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 1N hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give methyl (2Z)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylate as crystals (0.35 g, yield 95%) from a fraction eluted with hexane-ethyl acetate (4:1-1:1, v/v) (recrystallized from ethyl acetate-hexane). melting point: 108-109° C.

Workup

  1. temperatureto warm from −78° C. to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with 1N hydrochloric acid, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c8b7e21fd74f477c8b910c5ce184dcd9
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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