Water → HCID 23130438, compound

HRID 2080154Notes

Reaction equation

HRID 2080154 reaction equation
[Br:1][C:2]1[S:3][C:4](Br)=[CH:5][CH:6]=1.C([Li])CCC.[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]=[O:23])=[CH:21][C:16]=2[CH:15]=[CH:14]1.O>O1CCCC1>[O:13]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]([C:4]3[S:3][C:2]([Br:1])=[CH:6][CH:5]=3)[OH:23])=[CH:21][C:16]=2[CH:15]=[CH:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 184532,5-DibromothiopheneHCID 27738751-Benzofuran-5-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 23130438HCID 23130438, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,5-dibromothiophene (2.05 g, 8.48 mmol) in tetrahydrofuran (25 mL) was added n-butyl lithium (3.48 mL, 8.48 mmol) at −78° C., and the solution was stirred for 40 minutes. Then, benzofuran-5-carbaldehyde described in Preparation Example 175 (1.24 g, 8.48 mmol) was added to this reaction solution at −78° C., and the solution was stirred at room temperature for 75 minutes. Water was added to the reaction solution, which was then extracted with ethyl acetate, and the organic layer was washed with brine. Anhydrous magnesium sulfate was added to the organic layer for drying, which was then filtered, the filtrate was concentrated in vacuo, the residue was purified by NH silica gel column chromatography (heptane/ethyl acetate=3/1), and the title compound (2.11 g, 81%) was obtained as a light brown oil.

Workup

  1. additionwas added to this reaction solution at −78° C.
  2. stirringthe solution was stirred at room temperature for 75 minutes
  3. extractionwas then extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. additionAnhydrous magnesium sulfate was added to the organic layer
  6. customfor drying
  7. filtrationwhich was then filtered
  8. concentrationthe filtrate was concentrated in vacuo
  9. customthe residue was purified by NH silica gel column chromatography (heptane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-a39cbe6fab7b45b8bf8a65c3da9b855c
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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