Potassium Carbonate → HCID 86684884, compound

HRID 238386Notes

Reaction equation

HRID 238386 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[CH:14]=O)=[CH:4][CH:3]=1.[C:18](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-].C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[C:14]#[CH:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86684882HCID 86684882, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 86684884HCID 86684884, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-[(4-chlorobenzyl)oxy]-1-methyl-1H-pyrazol-4-carbaldehyde (125 mg), potassium carbonate (173 mg), dimethyl (1-diazo-2-oxopropyl)phosphonate (192 mg) and methanol (2.5 mL) was stirred at a room temperature for 24 hours. Thereafter, a saturated sodium hydrogencarbonate aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20 to 70:30), so as to obtain the title compound (76 mg) in the form of a light yellow oily substance.

Workup

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated saline
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. concentrationfollowed by vacuum concentration
  5. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20 to 70:30)

Sources & evidence

ORD record
ord-36e6c85e8e014fae9be8c38e6f250cb2
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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