2,6-Lutidine → 3,3,3-Trifluoropropyl trifluoromethanesulfonate

HRID 593477Notes

Reaction equation

HRID 593477 reaction equation
N1C(C)=CC=CC=1C.[O:9]([S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])S(C(F)(F)F)(=O)=O.[F:24][C:25]([F:30])([F:29])[CH2:26][CH2:27]O>C(Cl)Cl>[F:23][C:20]([F:21])([F:22])[S:17]([O:9][CH2:27][CH2:26][C:25]([F:30])([F:29])[F:24])(=[O:18])=[O:19]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1375123,3,3-Trifluoro-1-propanol

Product 1

HCID 141328493,3,3-Trifluoropropyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (−25° C.), stirred solution of 2,6-lutidine (18.38 mL, 158 mmol) in DCM (120 mL) was added Tf2O (24.88 mL, 147 mmol) over 3 min, and the mixture was stirred for 5 min. To the reaction mixture was added 3,3,3-trifluoropropan-1-ol (12 g, 105 mmol) over an interval of 3 min. After 2 hr, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was concentrated to half its volume, then purified by loading directly on a silica gel column (330 g ISCO) and the product was eluted with DCM to afford Intermediate S-5D (13.74 g, 53%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 4.71 (2 H, t, J=6.15 Hz), 2.49-2.86 (2 H, m).

Workup

  1. waitAfter 2 hr
  2. stirringstirred for 1 hr
  3. concentrationThe reaction mixture was concentrated to half its volume
  4. custompurified
  5. washthe product was eluted with DCM
  6. customto afford Intermediate S-5D (13.74 g, 53%) as a colorless oil

Sources & evidence

ORD record
ord-9521371080654ddbbadfe0bed396d594
Source dataset
uspto-grants-2016_01
Patent number
US09242940B2

Reaction notes

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