Water → HCID 12564772, compound

HRID 724499Notes

Reaction equation

HRID 724499 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][CH:16]([CH2:20][C:21]1[S:22][C:23]([CH3:26])=[CH:24][CH:25]=1)[C:17]([OH:19])=O.O>ClCCCl>[CH3:26][C:23]1[S:22][C:21]2[CH2:20][CH:16]([CH3:15])[C:17](=[O:19])[C:25]=2[CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14812Phosphorus oxide (P4O10)HCID 12564788HCID 12564788, compound

Product 1

HCID 12564772HCID 12564772, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
140 °C

Procedure

Under nitrogen atmosphere, a reactor was loaded with polyphosphoric acid (72.1 g) and phosphorus pentoxide (72.1 g, 0.51 mol) was added thereto and stirred at 140° C. for 1 hour. Then, a solution of 2-methyl-3-[5-methylthiophen-2-yl]propanoic acid (43.0 g, 0.23 mol) in 1,2-dichloroethane (75 mL) was added dropwise and stirred at 100° C. for 2 hours. The reaction mixture was added to iced water (1,000 mL) with stirring and after 30 minutes, extracted with chloroform to obtain an organic layer. The organic layer was washed with an aqueous saturated sodium carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a black oil. The oil was purified by silica gel chromatography (hexane/ethyl acetate=5/1) to obtain 2,5-dimethyl-5,6-dihydrocyclopenta[1,2-b]thiophen-4-one (32.6 g, 84.1%) as a reddish brown oil.

Workup

  1. additionwas added
  2. stirringstirred at 100° C. for 2 hours
  3. stirringwith stirring and after 30 minutes
  4. extractionextracted with chloroform
  5. customto obtain an organic layer
  6. washThe organic layer was washed with an aqueous saturated sodium carbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customto obtain a black oil
  10. customThe oil was purified by silica gel chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e0773c017e244efa84119350fe789aa6
Source dataset
uspto-grants-2006_11
Patent number
US07141690B2

Reaction notes

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