HCID 13784978, compound → HCID 14126642, compound

HRID 329445Notes

Reaction equation

HRID 329445 reaction equation
[CH3:1][O:2][C:3]([CH:5]([C:7]1[CH:8]=[CH:9][C:10]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH2:13][C:14](OC)=[O:15])[CH:12]=1)[CH3:6])=[O:4]>O>[O:15]=[C:14]1[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:18][C:10]2[CH:9]=[CH:8][C:7]([CH:5]([CH3:6])[C:3]([O:2][CH3:1])=[O:4])=[CH:12][C:11]=2[CH2:13]1

Participants

3

Reactant 1

HCID 13784978HCID 13784978, compound

Product 1

HCID 14126642HCID 14126642, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.5 g of methyl 5-(1-methoxycarbonylethyl)-2-phenylthiophenylacetate [dicarboxylic acid ester] obtained in Example 1-(3) and 5.3 g of polyphosphoric acid (116%) was stirred at a temperature of 60°-80° C. for 6 hours. The mixture was cooled, and to this was added a mixture of ice and water to decompose excessive polyphosphoric acid. The resulting mixture was extracted with ethyl acetate. The organic layer was separated and washed successively with saturated brine solution, aqueous saturated sodium hydrogen carbonate solution and saturated brine solution. The washed extract was dried over anhydrous sodium sulfate. The solvent was distilled off from the dried extract under reduced pressure, and then the residue was recrystallized from a mixture of benzene and hexane to obtain 0.4 g of methyl 2-(10,11-dihydro-10-oxodibenzo[b,f]thiepin-2-yl)propionate (yield 89%), m.p. 81.0°-82.0° C.

Workup

  1. temperatureThe mixture was cooled
  2. additionto this was added
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed successively with saturated brine solution, aqueous saturated sodium hydrogen carbonate solution and saturated brine solution
  6. extractionThe washed extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off from the dried
  9. extractionextract under reduced pressure
  10. customthe residue was recrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-fc800309d0e64155937b8549eeb6bdef
Source dataset
uspto-grants-1990_01
Patent number
US04891433

Reaction notes

Loading…