Acetic Anhydride → HCID 19092726, compound

HRID 487677Notes

Reaction equation

HRID 487677 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[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]([O:18][CH3:19])=[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 190928224-Tert-butyl-2-(2-formyl-4-methoxyphenoxymethyl)thiazole

Product 1

HCID 19092726HCID 19092726, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-tert-butyl-2-(2-formyl-4-methoxyphenoxymethyl)thiazole (3.23 g) and acetic anhydride (3.2 ml) in xylene (30 ml) was stirred at 140° C. for 14 hours. After being cooled, the resulting mixture was concentrated to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with toluene. The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-(5-methoxybenzofuran-2-yl)thiazole (2.40 g).

Workup

  1. temperatureAfter being cooled
  2. concentrationthe resulting mixture was concentrated
  3. customto give a syrup
  4. washeluted with toluene
  5. additionThe fractions containing object compound
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-477659efa06d49859f8c2be63ebebff8
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

Loading…