Sodium Hydroxide → 4-Tert-butyl-2-[5-(2-carboxy-2-methylpropyl)benzofuran-2-yl]thiazole

HRID 487685Notes

Reaction equation

HRID 487685 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][C:20]([CH3:26])([C:22]([O:24]C)=[O:23])[CH3:21])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[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][C:20]([C:22]([OH:24])=[O:23])([CH3:26])[CH3:21])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 190927974-Tert-butyl-2-[5-(2-methyl-2-methoxycarbonylpropyl)benzofuran-2-yl]thiazole

Product 1

HCID 190926904-Tert-butyl-2-[5-(2-carboxy-2-methylpropyl)benzofuran-2-yl]thiazoleYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-(2-methyl-2-methoxycarbonylpropyl)benzofuran-2-yl]thiazole (0.33 g) and 1N aqueous sodium hydroxide (2 ml) in methanol (5 ml) was stirred under reflux for 5 hours. After being cooled, the resulting mixture was concentrated under reduced pressure and adjusted to pH 6 with diluted aqueous hydrochloric acid. The resulting crystals were collected by filtration and washed with water to give 4-tert-butyl-2-[5-(2-carboxy-2-methylpropyl)benzofuran-2-yl]thiazole (0.28 g).

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter being cooled
  3. concentrationthe resulting mixture was concentrated under reduced pressure
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-6f94cfeac6e544aaa45211163c0c6fc8
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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