Benzoyl chloride → HCID 178490912, compound

HRID 47611

Reaction equation

HRID 47611 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([OH:13])=[CH:11][C:10]([CH3:14])=[N:9]2)=[CH:5][CH:4]=1.[OH-].[Ca+2].[OH-].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OCC)(=O)C.CCCCCC>O1CCOCC1.O>[OH:13][C:12]1[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=2)[N:9]=[C:10]([CH3:14])[C:11]=1[C:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:27]

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 6093208Calcium HydroxideHCID 21226206Ethyl acetate hexaneHCID 178490910HCID 178490910, compound

Product 1

HCID 178490912HCID 178490912, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution containing 1.0 g of 2-(4-methoxybenzyl)-5-methyl-2H-pyrazol-3-ol in 30 ml of dioxan was treated with 679 mg of calcium hydroxide and 800 μl of benzoyl chloride, then heated at 110° C. for 2 h. To the mixture was added 20 drops of water and the mixture heated for a further 2 h. The solvent was evaporated under reduced pressure and the residue partitioned between dichloromethane/10% citric acid. The organic phase was washed with brine, then dried over anhydrous magnesium sulphate, filtered and evaporated to give yellow oil. The oil was purified twice by flash chromatography on silica gel, initially using methanol/dichloromethane (1:49) to give a red solid, then ethyl acetate/hexane (1:1 to 2:1) for the elutions to give 400 mg of [5-hydroxy-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone as a yellow gum. Mass spectrum (ES) m/z 323 [M+H]+.

Workup

  1. temperaturethe mixture heated for a further 2 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue partitioned between dichloromethane/10% citric acid
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto give yellow oil
  9. customThe oil was purified twice by flash chromatography on silica gel, initially using methanol/dichloromethane (1:49)
  10. customto give a red solid

Sources & evidence

ORD record
ord-b57b2889c45d4f6bab0134cfbdabfb8e
Source dataset
uspto-grants-2004_03
Patent number
US06699887B2

Linked notes

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