p-Toluenesulfonic acid → 1-(3-Methanesulfonylphenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 842182ノート

反応式

HRID 842182 の反応式
Cl.[CH3:2][S:3]([C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9])(=[O:5])=[O:4].[CH2:13]([O:15][C:16](=[O:30])[CH:17]([C:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18][C:19](=O)[CH3:20])[CH3:14].C(N(CC)CC)C.CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C.C(Cl)(Cl)Cl>[CH2:13]([O:15][C:16]([C:17]1[CH:18]=[C:19]([CH3:20])[N:9]([C:8]2[CH:10]=[CH:11][CH:12]=[C:6]([S:3]([CH3:2])(=[O:4])=[O:5])[CH:7]=2)[C:22]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:30])[CH3:14]

参加物

7

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 27351793-(Methylsulfonyl)aniline hydrochlorideHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

生成物 1

HCID 102933431-(3-Methanesulfonylphenyl)-5-methyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

実験手順

3-Methylsulfonylaniline hydrochloride (5.8 mmol, 1.2 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (5.8 mmol, 144 g), triethylamine (5.8 mmol, 0.61 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The resulting oil was resuspended in chloroform, then washed with water, 5% sodium bicarbonate, and brine. The organic layer was dried over NaSO44, then the solids were separated and solvents removed under vacuum. The crude material was purified over silica to yield the named product (m.p. 131° C.-133° C.).

後処理

  1. temperatureheated
  2. temperatureunder reflux
  3. washwashed with water, 5% sodium bicarbonate, and brine
  4. customThe organic layer was dried over NaSO44
  5. customthe solids were separated
  6. customsolvents removed under vacuum
  7. customThe crude material was purified over silica

出典と根拠

ORDレコード
ord-0f86e40f09554b94a257b38169915d9b
出典データセット
uspto-grants-2002_04
特許番号
US06372777B1

反応ノート

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