Sodium Hydroxide → 5,6-dihydro-2-methyl-3-(4-(methylthio)benzoyl)-4H-cyclopenta[b]thiophene-6-carboxylic acid

HRID 2308998Notes

Reaction equation

HRID 2308998 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]([C:10]([O:12]CC)=[O:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[S:6][C:5]2[CH:7]([C:10]([OH:12])=[O:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:15](=[O:24])[C:16]1[CH:17]=[CH:18][C:19]([S:22][CH3:23])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13934075ethyl 5,6-dihydro-2-methyl-3-[4-(methyl-thio)benzoyl]-4H-cyclopenta[b]thiophene-6-carboxylate

Product 1

HCID 139340765,6-dihydro-2-methyl-3-(4-(methylthio)benzoyl)-4H-cyclopenta[b]thiophene-6-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 12.32 g (0.034 moles) sample of ethyl 5,6-dihydro-2-methyl-3-[4-(methyl-thio)benzoyl]-4H-cyclopenta[b]thiophene-6-carboxylate, the product of Example 1h., was dissolved in 200 ml of refluxing MeOH. 81.32 ml (0.044 moles) of 0.5M sodium hydroxide was added dropwise over 45 min. The reaction was stirred for an additional 20 min at reflux. The MeOH was evaporated in vacuo and the residue was poured into 3N hydrochloric acid and ice. A sticky solid was filtered off, washed with water and was taken up in Et2O. The ether was washed with brine and dried (MgSO4). Evaporation of the solvent gave a tan solid which was recrystallized from acetonitrile to give 10.00 g of 5,6-dihydro-2-methyl-3-(4-(methylthio)benzoyl)-4H-cyclopenta[b]thiophene-6-carboxylic acid (88%), mp 131°-133° C.

Workup

  1. customthe product of Example 1h.
  2. temperatureat reflux
  3. customThe MeOH was evaporated in vacuo
  4. additionthe residue was poured into 3N hydrochloric acid and ice
  5. filtrationA sticky solid was filtered off
  6. washwashed with water
  7. washThe ether was washed with brine
  8. dry with materialdried (MgSO4)
  9. customEvaporation of the solvent
  10. customgave a tan solid which
  11. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-3f4328463d784b15bfc2c3da6e499c07
Source dataset
uspto-grants-1987_09
Patent number
US04692460

Reaction notes

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