Diethyl Ether → HCID 67362031, compound

HRID 1183193Notes

Reaction equation

HRID 1183193 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[C:3](=[O:21])[CH2:4][O:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[N:9]=[C:8]([C:18]([OH:20])=[O:19])[CH:7]=1.[CH3:24][Mg]Br.C(OCC)C.C(Cl)Cl>C1COCC1.O.CC(=O)OCC>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:10]1[C:6]([O:5][CH2:4][C:3]([OH:21])([CH3:24])[C:2]([CH3:23])([CH3:22])[CH3:1])=[CH:7][C:8]([C:18]([OH:20])=[O:19])=[N:9]1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 67363376HCID 67363376, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67362031HCID 67362031, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

610 mg (1.9 mmol) of 5-(3,3-dimethyl-2-oxo-butoxy)-1-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid were dissolved in 20 ml of dry THF under argon and cooled to 0° C. 1.4 ml of a 3 M solution of methylmagnesium bromide in diethyl ether (4.2 mmol) were added over 10 min. The mixture was allowed to reach room temperature overnight and then diluted with 50 ml of water and 30 ml of EA. After phase separation, the aqueous phase was adjusted to pH=3 by addition of 1 M hydrochloric acid. The precipitate which formed was dissolved by addition of 40 ml of DCM, the organic phase was separated, dried over sodium sulfate and evaporated. 390 mg (61%) of the title compound were obtained.

Workup

  1. customAfter phase separation
  2. additionthe aqueous phase was adjusted to pH=3 by addition of 1 M hydrochloric acid
  3. customThe precipitate which formed
  4. customthe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-7070a1938f0e46f18e4811e583ab4075
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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