Water → HCID 54509660, compound

HRID 280591Notes

Reaction equation

HRID 280591 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[CH3:10][O:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]2[C:21]([CH2:22]Br)=[CH:20][S:19][C:18]=2[CH:24]=1)=[O:13].O>CN(C)C=O>[CH3:10][O:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]2[C:21]([CH2:22][O:3][C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)=[CH:20][S:19][C:18]=2[CH:24]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 54207325HCID 54207325, compound

Product 1

HCID 54509660HCID 54509660, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.12 g of 50% dispersion in mineral oil) was added to a solution of 3-hydroxypyridine (0.24 g) in dry N,N-dimethylformamide (5 ml) and the mixture was stirred for 30 minutes. 3-Bromomethylbenzo[b]thiophene-6-carboxylic acid methyl ester (0.71 g) in a small volume of N,N-dimethylformamide was added and the mixture was stirred at room temperature for 2 hours and then poured into water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave a gummy solid which was chromatographed on silica gel. Elution with chloroform first gave some impurity followed by pure product. Evaporation of the product containing fractions gave 3-(3-pyridyloxymethyl)benzo[b]thiophene-6-carboxylic acid methyl ester (0.27 g) which was used directly in the next stage.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionThe mixture was extracted several times with ethyl acetate
  3. washthe combined extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customgave a gummy solid which
  7. customwas chromatographed on silica gel
  8. washElution with chloroform
  9. customfirst gave some impurity
  10. customEvaporation of the product
  11. additioncontaining fractions

Sources & evidence

ORD record
ord-d27a5d5363f44fe89317fe7cbf5c8f9f
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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