Triethylamine → 2-Methyl-5-pyridinetrifluoromethanesulfonate

HRID 1034298Notes

Reaction equation

HRID 1034298 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.CCN(CC)CC.[O:16](S(C(F)(F)F)(=O)=O)[S:17]([C:20]([F:23])([F:22])[F:21])(=O)=[O:18]>C(Cl)Cl>[F:21][C:20]([F:23])([F:22])[S:17]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[N:4][CH:3]=1)(=[O:18])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 142752-Methyl-5-hydroxypyridineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 145472812-Methyl-5-pyridinetrifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5 g of 3-hydroxy-6-methylpyridine in 100 mL of CH2Cl2 at 0° C. was added successively 7.7 mL of Et3N and 8.1 mL of Tf2O. The reaction was stirred at room temperature for 30 minutes, then diluted with more CH2Cl2 (220 mL). The organic phase was washed successively with 1N HCl, brine, dried over MgSO4, filtered, and concentrated to give after purification using flash chromatography on silica gel (hexane:EtOAc 65:35) the title compound.

Workup

  1. washThe organic phase was washed successively with 1N HCl, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give
  6. customafter purification

Sources & evidence

ORD record
ord-f1fc0e9a1eb74871a6d4593a25beaf96
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

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