Water → 5-(3-Pyridylmethoxy)benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1583361Notes

Reaction equation

HRID 1583361 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[S:11][C:10]2[CH:12]=[CH:13][C:14]([OH:16])=[CH:15][C:9]=2[CH:8]=1)=[O:6].Cl[CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.O>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[S:11][C:10]2[CH:12]=[CH:13][C:14]([O:16][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:15][C:9]=2[CH:8]=1)=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 13662999Methyl 5-hydroxybenzo[b]thiophene-2-carboxylate

Product 1

HCID 544677875-(3-Pyridylmethoxy)benzo[b]thiophene-2-carboxylic acid methyl esterYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.24 g. of 50% dispersion in mineral oil) was added portionwise to a solution of 5-hydroxybenzo[b]thiophene-2-carboxylic acid methyl ester (1.04 g.) in dry N,N-dimethylformamide (10 ml.) and the mixture was stirred at room temperature for 30 minutes. 3-Chloromethylpyridine (0.65 g.) in dry N,N-dimethylformamide (5 ml.) was then added and the mixture was stirred at room temperature for 1 hour, 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 a solid which was washed with petrol and crystallized from isopropanol to give 5-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylic acid methyl ester (0.80 g.), m.p. 126°-127° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionThe mixture was extracted several times with ethyl acetate
  3. washthe combined extracts were washed well with water
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customgave a solid which
  7. washwas washed with petrol
  8. customcrystallized from isopropanol

Sources & evidence

ORD record
ord-801dfec56d964a97875599ef6e51f3f8
Source dataset
uspto-grants-1985_11
Patent number
US04551468

Reaction notes

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