Tetrahydrofuran → HCID 54428728, compound

HRID 377539Notes

Reaction equation

HRID 377539 reaction equation
[Cl-].[CH3:2][O:3][CH:4]=C1C=CC=CC1[PH+](C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.C([Li])CCC.[Cl:34][C:35]1[C:36]([N:45]2[C:49]([CH:50]=O)=[C:48]([C:52]#[N:53])[CH:47]=[N:46]2)=[N:37][N:38]([CH3:44])[C:39]=1[O:40][CH:41]([F:43])[F:42]>CCCCCC.C(OCC)(=O)C.O>[Cl:34][C:35]1[C:36]([N:45]2[C:49]([CH:50]=[CH:2][O:3][CH3:4])=[C:48]([C:52]#[N:53])[CH:47]=[N:46]2)=[N:37][N:38]([CH3:44])[C:39]=1[O:40][CH:41]([F:43])[F:42]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 15790818HCID 15790818, compoundHCID 67004918HCID 67004918, compoundHCID 178418339Butyllithium

Product 1

HCID 54428728HCID 54428728, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.9 g (8.4 mmol) methoxymethylene-triphenylphosphonium chloride is added to 10 ml tetrahydrofuran and 5.6 ml (9.0 mmol) of a 1,6 molar solution of butyl lithium in hexane is slowly added dropwise at 0° C. The orange-coloured solution is stirred for another 30 minutes and then 1.0 g (3.3 mmol) 1-(4chlor-5-difluormethoxy-1-methyl-3-pyrazolyl)-5-formyl-4-pyrazol-carbonitrile is slowly added dropwise. Stirring continues for 2 hours at room temperature. The reaction mixture is then added to water, shaken with ethyl acetate, dried over magnesium sulphate and concentrated. Purification is by column chromatography using a hexane/ethyl acetate mixture.

Workup

  1. additionis slowly added dropwise at 0° C
  2. stirringStirring
  3. waitcontinues for 2 hours at room temperature
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-96b7ceca82ec4d869d138d911018b07f
Source dataset
uspto-grants-2000_02
Patent number
US06028034

Reaction notes

Loading…