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

HRID 361912Notes

Reaction equation

HRID 361912 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ae8b452005014efca867f32430b0d26d
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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