Acetic Anhydride → 4-Tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole

HRID 487678Notes

Reaction equation

HRID 487678 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][C:13]=2[CH:20]=O)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)C)(=O)C>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:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][C:13]=3[CH:20]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 190927824-Tert-butyl-2-(2,4-diformylphenoxymethyl)thiazole

Product 1

HCID 196038064-Tert-butyl-2-(5-formylbenzofuran-2-yl)thiazoleYield 1,232.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-tert-butyl-2-(2,4-diformylphenoxymethyl)thiazole (0.95 g) and acetic anhydride (12.9 ml) in dried xylene (100 ml) was stirred at 130° C. for 27 hours. After being cooled, the resulting mixture was concentrated in reduced pressure to give a residue. The residue was crystallized with diisopropyl ether. The resulting crystals were collected by filtration and washed with diisopropyl ether to give 4-tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole (11.01 g).

Workup

  1. temperatureAfter being cooled
  2. concentrationthe resulting mixture was concentrated in reduced pressure
  3. customto give a residue
  4. customThe residue was crystallized with diisopropyl ether
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-b438139a8fce408ebc4524e60f554a70
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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