Water → HCID 53824054, compound

HRID 1583360Notes

Reaction equation

HRID 1583360 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:10][O:11][C:12]([C:14]1[S:18][C:17]2[CH:19]=[CH:20][C:21]([CH2:23]Br)=[CH:22][C:16]=2[CH:15]=1)=[O:13].O>CN(C)C=O>[CH3:10][O:11][C:12]([C:14]1[S:18][C:17]2[CH:19]=[CH:20][C:21]([CH2:23][O:1][C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[CH:22][C:16]=2[CH:15]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 13662981HCID 13662981, compound

Product 1

HCID 53824054HCID 53824054, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Hydroxypyridine (0.40 g.) was dissolved in dry N,N-dimethylformamide (10 ml.) and sodium hydride (0.20 g. of 50% dispersion in mineral oil) was added portionwise with stirring and the resulting mixture was stirred at room temperature for 30 minutes. 5-(Bromomethyl)benzo[b]thiophene-2-carboxylic acid methyl ester (1.20 g.) in a few mls of dry N,N-dimethylformamide was then added and the mixture was stirred at room temperature for 30 minutes, and then poured into water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed well with water and dried (Na2SO4). Evaporation of the solvent gave an oil which was chromatographed on silica gel. Elution with a mixture of chloroform and toluene (1:1) first gave mineral oil followed by pure product. Evaporation of the product-containing fractions gave a solid (0.40 g.) which was crystallized from isopropanol/petrol (b.p. 60°-80°) to give 5-(3-pyridyloxymethyl)benzo[b]thiophene-2-carboxylic acid methyl ester, m.p. 106°-107° C.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. extractionThe mixture was extracted several times with ethyl acetate
  4. washthe combined extracts were washed well with water
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent
  7. customgave an oil which
  8. customwas chromatographed on silica gel
  9. washElution
  10. additionwith a mixture of chloroform and toluene (1:1) first gave mineral oil
  11. customEvaporation of the product-containing fractions
  12. customgave a solid (0.40 g.) which
  13. customwas crystallized from isopropanol/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-0a0a2716a0d541b1a7147a85f5a1b74f
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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