Diethyl Ether → HCID 53782882, compound

HRID 1200055Notes

Reaction equation

HRID 1200055 reaction equation
Br[C:2]1[S:6][C:5]([CH:7]=[CH:8][C:9]2[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[S:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:18]COCC.C([Li])CCC.CI>O>[CH3:18][C:2]1[S:6][C:5]([CH:7]=[CH:8][C:9]2[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[S:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 53963715HCID 53963715, compoundHCID 178418339Butyllithium

Product 1

HCID 53782882HCID 53782882, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-70 °C

Procedure

To a chilled (-70° C.), stirred solution of 3-[2-(5-bromo-2-thienyl)ethenyl]-benzo[b]thiophene (5.00 g) and ether (250 ml) was added n-butyllithium (6.8 ml of a 2.5M solution in hexanes), under nitrogen, over 2 mins. The mixture was stirred and chilled for 1.5 hrs. Methyl iodide (8.83 g) was added, and the mixture was allowed to warm to ambient temperature, with stirring, overnight. Water (200 ml) was added. The mixture was agitated, and the organic phase was separated. The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by high performance liquid chromatography (silica gel, eluted with 10% dichloromethane in hexane). The appropriate fractions were combined and evaporated to yield 3.53 g (88%) of product, mp 62°-64° C.

Workup

  1. temperaturechilled for 1.5 hrs
  2. temperatureto warm to ambient temperature
  3. stirringwith stirring, overnight
  4. stirringThe mixture was agitated
  5. customthe organic phase was separated
  6. washThe organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by high performance liquid chromatography (silica gel, eluted with 10% dichloromethane in hexane)
  11. customevaporated

Sources & evidence

ORD record
ord-380caa3367f348d685e85f97bd6c0f32
Source dataset
uspto-grants-1990_02
Patent number
US04904674

Reaction notes

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