3-Thiophenecarboxaldehyde → HCID 586422, compound

HRID 2301807Notes

Reaction equation

HRID 2301807 reaction equation
[CH3:1]C(C)([O-])C.[K+].C[C:8](P(OC)(O)=O)([C:10]([O-:12])=[O:11])[CH3:9].[S:18]1[CH:22]=[CH:21][C:20](C=O)=[CH:19]1>C1COCC1>[S:18]1[CH:22]=[CH:21][C:20]([CH:9]=[CH:8][C:10]([O:12][CH3:1])=[O:11])=[CH:19]1

Participants

5

Reactant 3

HCID 681353-ThiophenecarboxaldehydeHCID 23665647Potassium tert-butoxideHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 586422HCID 586422, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of potassium t-butoxide (61.5 g, 0.55 mol) in THF (800 mL) was cooled in an ice bath and trimethylphosphonoacetate (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 mixture 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-6016d3c2cccf48ff90c179877b0bdee8
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

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