HCID 20377685, compound → HCID 20377699, compound

HRID 2052359Notes

Reaction equation

HRID 2052359 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([C:13]([C:15]3[CH:16]=[C:17]([CH:21]([CH2:26][CH3:27])[C:22]([O:24]C)=[O:23])[CH:18]=[CH:19][CH:20]=3)=[O:14])=[CH:12][C:7]=2[CH:6]=1)=[O:4]>[OH-].[K+]>[C:3]([C:5]1[S:9][C:8]2[S:10][C:11]([C:13]([C:15]3[CH:16]=[C:17]([CH:21]([CH2:26][CH3:27])[C:22]([OH:24])=[O:23])[CH:18]=[CH:19][CH:20]=3)=[O:14])=[CH:12][C:7]=2[CH:6]=1)([OH:4])=[O:2]

Participants

3

Reactant 1

HCID 20377685HCID 20377685, compound

Product 1

HCID 20377699HCID 20377699, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

Methyl 2-{3-(5-methoxycarbonyl-thieno[2,3-b]thien-2-yl)carbonyl-phenyl}butyrate (19.1 g), suspended in a mixture of potassium hydroxide pellets (16.6 g), distilled water (75 cc) and ethanol (200 cc), is stirred for 48 hours at a temperature of about 20° C. The resulting solution is diluted with distilled water (300 cc), washed three times with diethyl ether (total 600 cc), decolourizing charcoal (3 g) is added, and the solution is filtered and added dropwise to a 5 N aqueous solution of hydrogen chloride (100 cc) cooled in an ice bath, the rate of addition being regulated in such a way that the temperature of the mixture remains below 10° C. The resulting crystals are filtered off, washed three times with distilled water (total 150 cc) and dried under reduced pressure (20 mm Hg) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. 2-{3-(5-Carboxy-thieno[2,3-b]thien-2-yl)carbonyl-phenyl}butyric acid (15.8 g), melting at 240° C., is obtained.

Workup

  1. distillationdistilled water (75 cc) and ethanol (200 cc)
  2. additionThe resulting solution is diluted with distilled water (300 cc)
  3. washwashed three times with diethyl ether (total 600 cc)
  4. additionis added
  5. filtrationthe solution is filtered
  6. additionadded dropwise to a 5 N aqueous solution of hydrogen chloride (100 cc)
  7. temperaturecooled in an ice bath
  8. additionthe rate of addition
  9. customremains below 10° C
  10. filtrationThe resulting crystals are filtered off
  11. washwashed three times with distilled water (total 150 cc)
  12. dry with materialdried under reduced pressure (20 mm Hg) at a temperature of about 20° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-e4eb786ee4da4aa9b5d4310c4e641226
Source dataset
uspto-grants-1980_01
Patent number
US04183944

Reaction notes

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