Benzoyl chloride → HCID 178490912、化合物

HRID 47611

反応式

HRID 47611 の反応式
[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]

参加物

7

反応物 4

HCID 7412Benzoyl chlorideHCID 6093208Calcium HydroxideHCID 21226206Ethyl acetate hexaneHCID 178490910HCID 178490910、化合物

生成物 1

HCID 178490912HCID 178490912、化合物

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-b57b2889c45d4f6bab0134cfbdabfb8e
出典データセット
uspto-grants-2004_03
特許番号
US06699887B2

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