Iodoethane → Isopropyl 4-(3-chloro-2-thienyl)-1-ethyl-2-methyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate

HRID 329938Notes

Reaction equation

HRID 329938 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[C:12]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])=[C:11]([CH3:19])[NH:10][C:9]2[CH2:20][O:21][C:22](=[O:23])[C:8]1=2.[H-].[Na+].[CH2:26](I)[CH3:27]>CN(C)C=O>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[C:12]([C:13]([O:15][CH:16]([CH3:17])[CH3:18])=[O:14])=[C:11]([CH3:19])[N:10]([CH2:26][CH3:27])[C:9]2[CH2:20][O:21][C:22](=[O:23])[C:8]1=2

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13853275Isopropyl 4-(3-chloro-2-thienyl)-2-methyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]-pyridine-3-carboxylate

Product 1

HCID 13853276Isopropyl 4-(3-chloro-2-thienyl)-1-ethyl-2-methyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 mmol of isopropyl 4-(3-chloro-2-thienyl)-2-methyl-5-oxo-1,4,5,7-tetrahydrofuro[3.4-b]pyridine-3-carboxylate are dissolved in 25 ml of dimethylformamide and deprotonated with NaH, and 20 mmol of ethyl iodide are added. After the mixture has been stirred at room temperature for 1 hour, it is concentrated, water is added to the residue and the product is filtered off with suction and recrystallized from methanol.

Workup

  1. additionare added
  2. concentrationit is concentrated
  3. additionwater is added to the residue
  4. filtrationthe product is filtered off with suction
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a9bba68bd74e43c69c0dfd3570c7b02f
Source dataset
uspto-grants-1990_01
Patent number
US04894378

Reaction notes

Loading…