Hydrochloric Acid → ethyl 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetate

HRID 1295244ノート

反応式

HRID 1295244 の反応式
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][C:14]#N)[C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:24].[Na+].[O:26]1CC[CH2:28][CH2:27]1.Cl>C(O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][C:14]([O:26][CH2:27][CH3:28])=[O:24])[C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 693145121-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile

生成物 1

HCID 69422631ethyl 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetate収率 99%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetonitrile (13.0 g), 4N aqueous sodium hydroxide solution (100 ml), tetrahydrofuran (100 ml) and ethanol (100 ml) was refluxed for 3 days. After cooling, the mixture was neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. A mixture of the residue, ethyl iodide (5.2 ml), potassium carbonate (11.9 g) and N,N-dimethylformamide (100 ml) was stirred at room temperature for 3 hrs. The reaction solution was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 1-benzyl-3-benzyloxy-1H-pyrazol-4-ylacetate (14.9 g, yield 99%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

後処理

  1. temperaturewas refluxed for 3 days
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. additionA mixture of the residue, ethyl iodide (5.2 ml), potassium carbonate (11.9 g) and N,N-dimethylformamide (100 ml)
  8. additionThe reaction solution was poured into water
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-1bd52a7fd614467eb1dbd7d4a8394be4
出典データセット
uspto-grants-2007_07
特許番号
US07241785B2

反応ノート

読み込み中…