Sodium hydride → Methyl-3-methyl-5-[3-(2quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylate

HRID 2248904Notes

Reaction equation

HRID 2248904 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[H-].[Na+].[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[CH2:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Cl>CN(C=O)C>[CH3:13][O:12][C:10]([C:7]1[S:6][C:5]2[CH:14]=[CH:15][C:2]([O:1][CH2:33][C:32]3[CH:35]=[CH:36][CH:37]=[C:30]([O:29][CH2:28][C:19]4[CH:20]=[CH:21][C:22]5[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:18]=4)[CH:31]=3)=[CH:3][C:4]=2[C:8]=1[CH3:9])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 145017062-(3-Chloromethylphenoxy)methylquinolineHCID 19994682Methyl 5-hydroxy-3-methylbenzo(b)thiophene-2-carboxylate

Product 1

HCID 54370568Methyl-3-methyl-5-[3-(2quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 5-hydroxy-3-methyl-benzo(b)thiophene-2-carboxylate (878.6 mg, 3.96 mmol) in dry DMF (20 ml) at room temperature is added sodium hydride (158 mg, 3.95 mmol) as a 60% dispersion in mineral oil. After 30 minutes of stirring 3-(2-quinolinylmethoxy)benzyl chloride (1.02 g, 3.60 mmol) is added. The solution is stirred at room temperature for 4 hours and quenched with ice-water. Extraction with ethyl acetate, washing with aqueous sodium carbonate, water and brine is followed by drying (MgSO4) and concentration. The residue is subjected to flash chromatography on silica gel. Elution with 25% ether in hexane affords methyl-3-methyl-5-[3-(2-quinolinylmethoxy)benzyloxy]benzo(b) -thiophene-2-carboxylate.

Workup

  1. customquenched with ice-water
  2. extractionExtraction with ethyl acetate
  3. washwashing with aqueous sodium carbonate, water and brine
  4. customby drying
  5. concentration(MgSO4) and concentration
  6. washElution with 25% ether in hexane

Sources & evidence

ORD record
ord-c0e7d9106c634bb68877df1a6a62d236
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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