Potassium Carbonate → 1-[(4-methoxyphenyl)methyl]-1H-pyrazole-4-carboxylic acid

HRID 928385ノート

反応式

HRID 928385 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]([O:8]CC)=[O:7])[CH:3]=[N:2]1.C([O-])([O-])=O.[K+].[K+].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.[OH-].[K+]>CC(C)=O.CCO>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:2]2[CH:3]=[C:4]([C:6]([OH:8])=[O:7])[CH:5]=[N:1]2)=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 1650214-Methoxybenzyl bromide

生成物 1

HCID 435653621-[(4-methoxyphenyl)methyl]-1H-pyrazole-4-carboxylic acid

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

A mixture of ethyl 1H-pyrazole-4-carboxylate (400 mg, 2.85 mmol), K2CO3 (1.97 g, 14.3 mmol) and 4-methoxybenzyl bromide (0.453 ml, 3.14 mmol) in dry acetone (10 ml) was heated to 50° C. for 3 h. The reaction mixture was filtered, and the filtrate was concentrated. EtOH (10 mL) and KOH (320 mg, 5.71 mmol) were added and the mixture was heated to 65° C. for 6 h, before it was concentrated again. The crude product was dissolved in water (5 ml), washed with EA (2×10 ml) and acidified with 1N HCl. The resulting precipitate was collected by filtration, washed with water and dried in vacuo affording the title compound. LCMS RtL=0.86 min, [M+H]+=233.2.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. temperaturethe mixture was heated to 65° C. for 6 h, before it
  4. concentrationwas concentrated again
  5. dissolutionThe crude product was dissolved in water (5 ml)
  6. washwashed with EA (2×10 ml)
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with water
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-ece42cd380174cfb9d74d6cf022a47fb
出典データセット
uspto-grants-2016_03
特許番号
US09290485B2

反応ノート

読み込み中…