Sodium hydride → HCID 69411214, compound

HRID 857471Notes

Reaction equation

HRID 857471 reaction equation
[H-].[Na+].[Cl-:3].[CH3:4][Si:5]([CH3:30])([CH3:29])[CH2:6][CH2:7][O:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:31]([O:33][C:34]([C:36]1[C:40]([CH:41]=O)=[C:39]([C:43]2[CH:48]=[CH:47][C:46](Cl)=[CH:45][CH:44]=2)[N:38]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2Cl)N=1)=[O:35])[CH3:32].[Cl-:57].[NH4+:58]>CS(C)=O>[CH2:31]([O:33][C:34]([C:36]1[C:40]([CH:41]=[CH:9][O:8][CH2:7][CH2:6][Si:5]([CH3:30])([CH3:29])[CH3:4])=[C:39]([C:43]2[CH:48]=[CH:47][C:46]([Cl:3])=[CH:45][CH:44]=2)[N:38]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][C:51]=2[Cl:57])[N:58]=1)=[O:35])[CH3:32]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11396265Triphenyl{[2-(trimethylsilyl)ethoxy]methyl}phosphanium chlorideHCID 58763926HCID 58763926, compound

Product 1

HCID 69411214HCID 69411214, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A slurry of sodium hydride (45 mg of 60% in oil) in dimethyl sulfoxide (2 ml) was stirred at 75° C. for 45 minutes, cooled to room temperature, then (2-(trimethylsilyl)-ethoxymethyl)triphenylphosphonium chloride (480 mg) was added in one portion to produce a red solution. After 10 minutes, a solution of 5-(4-chloro-phenyl)-1-(2-chloro-phenyl)-4-formyl-1H-pyrazole-3-carboxylic acid ethyl ester (218 mg) in dimethylsulfoxide (1 ml) was added dropwise and the resulting solution was stirred for 1 hour. Saturated aqueous ammonium chloride was added and the reaction mixture was partitioned between diethyl ether and water. The organic phase was dried (Na2SO4) and concentrated in vacuo to afford a purple oil. Silica gel chromatography (30% ethyl acetate/hexanes) afforded the title compound (I-3a) as a golden oil, 210 mg.

Workup

  1. customto produce a red solution
  2. customthe reaction mixture was partitioned between diethyl ether and water
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto afford a purple oil

Sources & evidence

ORD record
ord-0ae90b3df4e6460483f88e16c7a1f241
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

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