2-Thiophenecarboxaldehyde → HCID 53692472, compound

HRID 1871454Notes

Reaction equation

HRID 1871454 reaction equation
[H-].[Na+].CCCCCC.[CH3:9][CH2:10][O:11][C:12]([CH:14](P(OCC)(OCC)=O)[CH3:15])=[O:13].[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH:29]=O>O1CCCC1.O>[CH3:15][C:14](=[CH:29][C:25]1[S:24][CH:28]=[CH:27][CH:26]=1)[C:12]([O:11][CH2:10][CH3:9])=[O:13]

Participants

7

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 8058HexaneHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionate

Product 1

HCID 53692472HCID 53692472, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.1 g of sodium hydride in oil (prewashed by decantation with hexane.) in 60 ml of dry tetrahydrofuran was added dropwise 30 g of triethyl 2-phosphonopropionate over a period of 30 minutes under dry argon atmosphere at room temperature. After the mixture was stirred for further 1 hour, a solution of 11.8 g of 2-thiophenealdehyde in 30l of tetrahydrofuran was added dropwise. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed successively with water and saturated saline, dried over anhydrous magnesium sulfate. Drying agent was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel to give 11.0 g of ethyl 2-methyl-3-(2-thienyl)acrylate as a yellow oil. Next, 150 ml of ethanol and 60 ml of aqueous 2N sodium hydroxide were added to the oil, and the mixture was refluxed for 1 hour. After cooling, ethanol was removed under reduced pressure, and the residue was acidified with dilute hydrochloric acid. Crystalline precipitate was collected by filtration to give 8.2 g of 2-methyl-3-(2-thienyl)acrylic acid as a white powder.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customDrying agent
  6. customwas removed by filtration
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e702fba584fb430bb8f12316f819e2ff
Source dataset
uspto-grants-2000_08
Patent number
US06103736

Reaction notes

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