Tetrahydrofuran → HCID 586422, compound

HRID 1862725Notes

Reaction equation

HRID 1862725 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[S:7]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[CH:8]1.C1C[O:17][CH2:16]C1>>[S:7]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:5][C:2]([O:17][CH3:16])=[O:4])=[CH:8]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 681353-ThiophenecarboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 586422HCID 586422, compound

Procedure

A suspension of potassium t-butoxide (61.5 g, 0.55 mol) in THF (800 mL) was cooled in an ice bath and trimethylphospbonoacetate (98 mL, 0.60 mol) in THF (100 mL) was slowly added. After 45 min, thiophene 3-carboxaldehyde (50 mL, 0.55 mol) in THF (100 mL) was slowly added while stirred in the ice bath. The mi,suture was allowed to warm to rt and stirred for 16 h. The reaction was quenched with 5% sulfuric acid (300 mL) and extracted twice with ether. The organic layers were each washed with brine, dried over magnesium sulfate, combined and concentrated. The residue was purified by FC (10% ethyl acetate in hexanes) and then crystallized from hexanes to give the title compound (71.3 g).

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe reaction was quenched with 5% sulfuric acid (300 mL)
  3. extractionextracted twice with ether
  4. washeach washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by FC (10% ethyl acetate in hexanes)
  8. customcrystallized from hexanes

Sources & evidence

ORD record
ord-0de1b2d591174c5b97185d9416623462
Source dataset
uspto-grants-2003_03
Patent number
US06538002B1

Reaction notes

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