4-Tert-butyl-2-[5-(2,2-diethoxycarbonylethyl)benzofuran-2-yl]thiazole → 4-Tert-butyl-2-[5-(2,2-dicarboxyethyl)benzofuran-2-yl]thiazole

HRID 487704Notes

Reaction equation

HRID 487704 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([C:26]([O:28]CC)=[O:27])[C:21]([O:23]CC)=[O:22])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>Cl>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([C:21]([OH:23])=[O:22])[C:26]([OH:28])=[O:27])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 190926974-Tert-butyl-2-[5-(2,2-diethoxycarbonylethyl)benzofuran-2-yl]thiazole

Product 1

HCID 190927654-Tert-butyl-2-[5-(2,2-dicarboxyethyl)benzofuran-2-yl]thiazoleYield 27.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-(2,2-diethoxycarbonylethyl)benzofuran-2-yl]thiazole (3.99 g) and conc. hydrochloric acid (20 ml) was stirred under reflux for 6 hours. After being cooled, the resulting mixture was extracted with ethyl acetate. The extract was allowed to stand until there were no further precipitates separated out. The precipitates were collected by filtration and washed with ethyl acetate to give 4-tert-butyl-2-[5-(2,2-dicarboxyethyl)benzofuran-2-yl]thiazole (0.96 g).

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureAfter being cooled
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. customno further precipitates
  5. customseparated out
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-79e832f0fa3b43a795750c260e9bf939
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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