Dimethylformamide → HCID 68546537, compound

HRID 2243494Notes

Reaction equation

HRID 2243494 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[C:10]3[C:15]([CH:16]=[CH:17][C:7]=2[C:6]=1[OH:18])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[C:10]3[C:15]([CH:16]=[CH:17][C:7]=2[C:6]=1[O:18][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 68547888HCID 68547888, compound

Product 1

HCID 68546537HCID 68546537, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an oven-dried 50 mL round bottom flask under a nitrogen atmosphere was added 3-hydroxy-naphtho[1,2-b]thiophene-2-carboxylic acid methyl ester (0.134 g, 052 mmol), ethyl bromoacetate (0.06 mL, 052 mmol), potassium carbonate (0.072 g, 052 mmol) and 20 mL DMF. The resulting mixture was allowed to stir for 16 hours at room temperature. 30 mL water was added to the mixture, at which point a precipitate formed. The solids were collected by filtration and dried in vacuo. 3-ethoxycarbonylmethoxy-naphtho[1,2-b]thiophene-2-carboxylic acid methyl ester was isolated as a white solid (0.116 g, 65%).

Workup

  1. customformed
  2. filtrationThe solids were collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a2cda408bdf141d9be14d6ffd8f40773
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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