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

HRID 53977

반응식

HRID 53977 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dbde7cd1490149faa0abad586b4db122
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620991

연결된 노트

불러오는 중…