Water → 1H-Pyrazole-1-carboxylic acid, 4,5-dihydro-5-phenyl-, ethyl ester

HRID 981176

反応式

HRID 981176 の反応式
C(N(CC)CC)C.[C:8]1([CH:14]2[NH:18][N:17]=[CH:16][CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].O>C(Cl)(Cl)Cl>[CH2:23]([O:22][C:20]([N:18]1[CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:15][CH:16]=[N:17]1)=[O:21])[CH3:24]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1208415-Phenyl-4,5-dihydro-1H-pyrazole

生成物 1

HCID 30790771H-Pyrazole-1-carboxylic acid, 4,5-dihydro-5-phenyl-, ethyl ester収率 62%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

Triethylamine (2.1 g) was added to a solution of 2.92 g 5-phenyl-2-pyrazoline in 50 ml chloroform, and the mixture was stirred with ice cooling. To the resulting solution, was added dropwise 2.17 g ethyl chloroformate, and the mixture was stirred for one hour. After addition of 50 ml water, the mixture was extracted with 50 ml chloroform, the extract was dried, the dried solution was concentrated, and the residue was purified by silica gel chromatography (chloroform/methanol=100/1), giving 2.7 g (yield: 62%) of pure product as oil. NMR (DMSO-d6): 1.21 (3H, t, J=6 Hz), 2.6-3.7 (2H, m), 4.18 (2H, q, J=6 Hz), 5.22 (1H, dd, J=6, 12 Hz), 6.92 (1H, t, J=2 Hz), 7.1-7.5 (5H, m).

後処理

  1. stirringthe mixture was stirred for one hour
  2. extractionthe mixture was extracted with 50 ml chloroform
  3. customthe extract was dried
  4. concentrationthe dried solution was concentrated
  5. customthe residue was purified by silica gel chromatography (chloroform/methanol=100/1)

出典と根拠

ORDレコード
ord-3bad1db943884d71a99e043437695970
出典データセット
uspto-grants-1991_02
特許番号
US04990529

関連ノート

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