Pyridine → 32264-79-2

HRID 247858Notes

Reaction equation

HRID 247858 reaction equation
N1C=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].C(O)CC#C.CCCCC>C(Cl)Cl>[O:12]([CH2:2][CH2:3][C:4]#[CH:5])[S:9]([C:8]([F:21])([F:20])[F:7])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8003PentaneHCID 135663-Butyn-1-OLHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 1976466532264-79-2Yield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The compound was prepared following a procedure of Hummel et al. Liebigs Ann. Chem. 746, 211-213 (1971). Anhydrous pyridine (20.0 mL, 19.6 g, 0.248 mol) was added to a stirred solution of trifluoromethanesulfonic anhydride (70.0 g, 0.248 mol) in anhydrous CH2Cl2 (500 mL) at 0° C. over a dry nitrogen atmosphere in an oven-dried apparatus. A heavy white precipitate formed immediately, and the resulting slurry was stirred for 15 min at 0° C. A solution of 3-butyn-1-ol (16.6 g, 0.236 mol) in anhydrous CH2Cl2 (80 mL) was added dropwise at 0° C. The slurry was warmed to room temperature and stirred for 2 h. Pentane (1000 mL) was added and the precipitated salts were filtered and washed with pentane. Fractional distillation of the combined filtrates gave 39.9 g (84% yield) of 3-butynyl triflate as a colorless liquid:

Workup

  1. customThe compound was prepared
  2. customA heavy white precipitate formed immediately
  3. temperatureThe slurry was warmed to room temperature
  4. stirringstirred for 2 h
  5. filtrationthe precipitated salts were filtered
  6. washwashed with pentane
  7. distillationFractional distillation of the combined filtrates

Sources & evidence

ORD record
ord-f43525de48f147d4a0098463ddea52a1
Source dataset
uspto-grants-1993_05
Patent number
US05208244

Reaction notes

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