2,6-Lutidine → 2-(3-Methoxyphenyl)oxazol-4-yl trifluoromethanesulfonate

HRID 643642Notes

Reaction equation

HRID 643642 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:10][CH2:11][C:12](=[O:14])[N:13]=2)[CH:6]=[CH:7][CH:8]=1.N1C(C)=CC=CC=1C.[O:23](S(C(F)(F)F)(=O)=O)[S:24]([C:27]([F:30])([F:29])[F:28])(=O)=[O:25]>C(Cl)Cl>[F:28][C:27]([F:30])([F:29])[S:24]([O:14][C:12]1[N:13]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[O:10][CH:11]=1)(=[O:25])=[O:23]

Participants

5

Reactant 3

HCID 79372,6-Lutidine2×HCID 67749Trifluoromethanesulfonic anhydride2×HCID 592629642-(3-methoxyphenyl)oxazol-4(5H)-one

Product 1

HCID 592629762-(3-Methoxyphenyl)oxazol-4-yl trifluoromethanesulfonateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 16 (516 mg, 1 eq) was dissolved in CH2Cl2. To the resulting solution, at 0° C., was added 501 μL (1.6 eq) of 2,6-lutidine, followed by the dropwise addition of Tf2O (681 ml, 1.5 eq). The resulting mixture was stirred for 4 h at RT, then an additional 501 μL (1.6 eq) of 2,6-lutidine and 681 ml (1.5 eq) of Tf2O were added. After 1 h, the mixture was evaporated and the residue purified by flash chromatography (SiO2, CH2Cl2/hexane, 9/1) giving 17 as a red oil in 75% yield.

Workup

  1. waitAfter 1 h
  2. customthe mixture was evaporated
  3. customthe residue purified by flash chromatography (SiO2, CH2Cl2/hexane, 9/1)

Sources & evidence

ORD record
ord-640e49137c154ada8ab3681e2d7d2d88
Source dataset
uspto-grants-2010_04
Patent number
US07700616B2

Reaction notes

Loading…