Tetrahydrofuran → HCID 19759295, compound

HRID 1586824Notes

Reaction equation

HRID 1586824 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[O:17]1CCC[CH2:18]1.C([Li])CCC>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[C:9]=2[CH:18]=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4137393Benzo[b]thiophene, 2-(4-methylphenyl)-HCID 178418339Butyllithium

Product 1

HCID 19759295HCID 19759295, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-(4-methylphenyl)benzo[b]thiophene (896 mg) in freshly distillated tetrahydrofuran (15 ml) was added n-butyllithium (2.75 ml, 1.6 mol solution in n-hexane) through a syringe at -78° C. The solution was stirred at -78° C. for 10 minutes and then at ambient temperature for half an hour. To the deep red colored solution was added N,N-dimethylformamide (365mg) at 5° C. The mixture was stirred at ambient temperature for one hour, quenched with aqueous saturated ammonium chloride solution, and extracted with diethyl ether. The organic layer was washed with aqueous saturated ammonium chloride solution, dried, and concentrated in vacuo to give a yellow residue, which was purified by flash column chromatography on silica gel eluted with 50% n-hexane in dichloromethane to yield 2-(4-methylphenyl)benzo[b]thiophene-3-carbaldehyde (285 mg) as white crystals.

Workup

  1. waitat ambient temperature for half an hour
  2. stirringThe mixture was stirred at ambient temperature for one hour
  3. customquenched with aqueous saturated ammonium chloride solution
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with aqueous saturated ammonium chloride solution
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customto give a yellow residue, which
  9. customwas purified by flash column chromatography on silica gel
  10. washeluted with 50% n-hexane in dichloromethane

Sources & evidence

ORD record
ord-19ab70f4917b4ca7a518ef753b060680
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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