Trimethylsilyldiazomethane → HCID 178498885, compound

HRID 1842563Notes

Reaction equation

HRID 1842563 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([OH:14])=[O:13])=[CH:10][NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[C:1]1([C:7]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][NH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 178524802HCID 178524802, compound

Product 1

HCID 178498885HCID 178498885, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-phenyl-1H-pyrazole-4-carboxylic acid (1.0 g, 5.31 mmol) in dichloromethane (14.2 mL) and methanol (3.5 mL) was added trimethylsilyldiazomethane (2.66 mL, 5.31 mmol). The mixture was stirred at ambient temperature. After 30 min, additional trimethylsilyldiazomethane (0.80 mL, 1.59 mmol) was added. After 10 min, the mixture was concentrated. Purification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol) gave the title compound (0.9 g). MS 203.1 (M+1).

Workup

  1. waitAfter 10 min
  2. concentrationthe mixture was concentrated
  3. customPurification by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol)

Sources & evidence

ORD record
ord-c7d56a7c1dfc42b89ff98199f5497afc
Source dataset
uspto-grants-2015_02
Patent number
US08946231B2

Reaction notes

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