HCID 19092743, compound → HCID 19092778, compound

HRID 487702Notes

Reaction equation

HRID 487702 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]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][CH:28](C(O)=O)[C:29]([OH:31])=[O:30])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C1(C)C(C)=CC=CC=1>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 19092743HCID 19092743, compound

Product 1

HCID 19092778HCID 19092778, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-{2-(2,2-dicarboxyethyl)phenylmethoxy}benzofuran-2-yl]thiazole (1.30 g) in xylene (20 ml) was refluxed with stirring for 7 hours. After being cooled, the mixture was subjected to column chromatography on silica gel (45 g) and eluted with a mixture of methanol and chloroform. The fractions containing object compound were combined and concentrated under reduced pressure. The residue was recrystallized from a mixture of diethyl ether and petroleum ether to give 4-tert-butyl-2-[5-{2-(2-carboxyethyl)phenylmethoxy}benzofuran-2-yl]thiazole (0.86 g).

Workup

  1. temperaturewas refluxed
  2. temperatureAfter being cooled
  3. washeluted with a mixture of methanol and chloroform
  4. additionThe fractions containing object compound
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from a mixture of diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-44cdb33dbbd2425196c9b9445c155d76
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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