Ammonium Chloride → HCID 86644482, compound

HRID 2404549Notes

Reaction equation

HRID 2404549 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N:15]1[C:19]([C:20](OCC)=[O:21])=[CH:18][C:17]([O:25][C:26]([F:35])([F:34])[CH:27]([F:33])[O:28][C:29]([F:32])([F:31])[F:30])=[N:16]1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH:20]([C:19]1[N:15]([C:3]2[CH:4]=[C:5]([S:9][CH2:10][C:11]([F:14])([F:13])[F:12])[C:6]([CH3:8])=[CH:7][C:2]=2[F:1])[N:16]=[C:17]([O:25][C:26]([F:35])([F:34])[CH:27]([F:33])[O:28][C:29]([F:30])([F:31])[F:32])[CH:18]=1)=[O:21]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 86644483HCID 86644483, compound

Product 1

HCID 86644482HCID 86644482, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.1 g of ethyl 1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole-5-carboxylate was dissolved in 30 mL of toluene, followed by cooling to −78° C., and 2.6 mL of a toluene solution (1.0 mol/L) of diisobutyl aluminum hydride was slowly dropwise added. After stirring for 3 hours, a saturated aqueous solution of ammonium chloride was added, extraction with ethyl acetate was carried out, the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:3) to obtain 0.95 g of 5-formyl-1-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl}-3-{1,1,2-trifluoro-2-(trifluoromethoxy)ethoxy}pyrazole (1H-NMR (CDCL3/TMS δ (ppm) value) δ: 2.56 (3H, s), 3.39 (2H, q), 6.05 (1H, dt), 6.85 (1H, s), 7.17 (1H, d), 7.66 (1H, d), 9.72 (1H, d)).

Workup

  1. extractionextraction with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe obtained residue was purified by column chromatography (developing solvent ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-8d6b99e9af6b40c1ab16a8d5daa9b884
Source dataset
uspto-grants-2014_08
Patent number
US08802713B2

Reaction notes

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