Hydrochloric Acid → HCID 15124021, compound

HRID 1084869Notes

Reaction equation

HRID 1084869 reaction equation
[OH-].[K+].C(OC([C:8]1[O:9][C:10]2[C:17]([C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[O:19])=[CH:16][C:15]([C:25]([CH3:28])([CH3:27])[CH3:26])=[C:14]([OH:29])[C:11]=2[C:12]=1[CH3:13])=O)C.Cl>O.CO>[CH3:13][C:12]1[C:11]2[C:14]([OH:29])=[C:15]([C:25]([CH3:27])([CH3:26])[CH3:28])[CH:16]=[C:17]([C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[O:19])[C:10]=2[O:9][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15124019HCID 15124019, compound2×

Product 1

HCID 15124021HCID 15124021, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of KOH (0.18 g, 3.21 mmol) in 8.0 mL water and 3.0 mL methanol was added ethyl-3-methyl-4-hydroxy-5-tert-butyl-7-(2-thienoyl)-benzofuran-2-carboxylate, compound 13 (0.412 g, 1.07 mmol). The reaction mixture was heated to reflux for 0.5 hours. The resulting solution was cooled in an ice bath and acidified by the dropwise addition of 2N HCl. The acid was collected by filtration, washed with water and pulled dry over night on the filter funnel to give desired product sufficiently pure for further use. mp 145° C. with decarboxylation; 1H NMR (DMSO-d6) d 1.44 (9H, s), 2.76 (3H, s), 7.17 (1H, dd, J=4 Hz), 7.73 (2H, d, J=4 Hz), 7.90 (1H, s).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 0.5 hours
  3. temperatureThe resulting solution was cooled in an ice bath
  4. filtrationThe acid was collected by filtration
  5. washwashed with water
  6. custompulled dry over night on the filter funnel

Sources & evidence

ORD record
ord-bf6208d765c345c6a81a1adadc9636ff
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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