2,6-Lutidine → 2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yl trifluoromethanesulfonate

HRID 1604647Notes

Reaction equation

HRID 1604647 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.O[C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23]([C:25]3[S:26][CH:27]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[N:29]=3)=[CH:22][C:21]=2[CH:34]=1.N1C(C)=CC=CC=1C>ClCCl>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23]([C:25]3[S:26][CH:27]=[C:28]([C:30]([CH3:32])([CH3:31])[CH3:33])[N:29]=3)=[CH:22][C:21]=2[CH:34]=1)(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 108586652-(4-Tert-butylthiazol-2-yl)-5-hydroxybenzofuran

Product 1

HCID 196036842-(4-Tert-butylthiazol-2-yl)benzofuran-5-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.74 ml) was added dropwise to an ice-cooled mixture of 2-(5-hydroxy-benzofuran-2-yl)-4-tert-butylthiazole (1.0 g), N,N-dimethylaminopyridine (67 mg) and 2,6-lutidine (0.52 ml, 4.39 mmol) in dry dichloromethane (10 ml) below 10° C. After being stirred at room temperature for 2 hours, the reaction mixture was washed with diluted hydrochloric acid, then dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using n-hexane-ethyl acetate (4:1) as eluent to give 2-(4-tert-butylthiazol-2-yl)-benzofuran-5-yl trifluoromethanesulfonate as a colorless oil (1.39 g).

Workup

  1. temperaturecooled
  2. washthe reaction mixture was washed with diluted hydrochloric acid
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-179a422cf5dc4871b9afcf460a195431
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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