Sodium hydride → Ethyl 3-(5-bromobenzo[b]thien-2-yl)-2-ethoxycarbonyl-2-(4-methoxyphenyl)propionate

HRID 1738690

反応式

HRID 1738690 の反応式
[CH2:1]([O:3][C:4]([CH:6]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])[CH3:2].[H-].[Na+].[Br:22][C:23]1[CH:33]=[CH:32][C:26]2[S:27][C:28]([CH2:30]Br)=[CH:29][C:25]=2[CH:24]=1.[Cl-].[NH4+]>O1CCCC1>[Br:22][C:23]1[CH:33]=[CH:32][C:26]2[S:27][C:28]([CH2:30][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:29][C:25]=2[CH:24]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2785178Diethyl 2-(4-methoxyphenyl)malonateHCID 148193525-Bromo-2-(bromomethyl)benzo[b]thiophene

生成物 1

HCID 21844202Ethyl 3-(5-bromobenzo[b]thien-2-yl)-2-ethoxycarbonyl-2-(4-methoxyphenyl)propionate収率 92.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

14.2 g of ethyl 2-ethoxycarbonyl-2-(4-methoxyphenyl)acetate was dissolved in 150 ml of tetrahydrofuran. 2.6 g of sodium hydride (oil type, 60%) was added to the above solution while stirring under ice cooling, and the stirring was continued for 20 minutes. To this was further added 17.2 g of 5-bromo-2-bromomethylbenzo[b]thiophene. After stirring at room temperature for 18 hours, the resulting reaction solution was mixed with ammonium chloride aqueous solution, and then extracted with ethyl acetate. After drying to distill off the solvent, the resulting residue was subjected to silica gel column chromatography using chloroform as an elution solvent, thereby obtaining 24.2 g of ethyl 3-(5-bromobenzo[b]thien-2-yl)-2-ethoxycarbonyl-2-(4-methoxyphenyl)propionate.

後処理

  1. stirringAfter stirring at room temperature for 18 hours
  2. customthe resulting reaction solution
  3. extractionextracted with ethyl acetate
  4. customAfter drying
  5. distillationto distill off the solvent

出典と根拠

ORDレコード
ord-ca7c9e718b2349fc8e3638ca0ba62a0b
出典データセット
uspto-grants-1999_10
特許番号
US05962695

関連ノート

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