Methyl triflate → HCID 13765568, compound

HRID 1731403Notes

Reaction equation

HRID 1731403 reaction equation
F[C:2](F)(F)S(OC)(=O)=O.[F:10][C:11]([F:24])([C:13]([F:23])([O:18][C:19]([F:22])([F:21])[F:20])[C:14]([F:17])([F:16])[F:15])[O-:12].CN([S+](N(C)C)N(C)C)C>C(#N)C1C=CC=CC=1>[F:10][C:11]([O:12][CH3:2])([F:24])[C:13]([F:23])([O:18][C:19]([F:20])([F:22])[F:21])[C:14]([F:17])([F:16])[F:15]

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 20225804HCID 20225804, compound

Product 1

HCID 13765568HCID 13765568, compound

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

Methyl trifluoromethanesulfonate, 8.53 g (0.052 mol), was added dropwise to a stirred solution of 23.0 g (0.055 mol) of tris(dimethylamino)sulfonium 1,1,2,3,3,3-hexafluoro-2-(trifluoromethoxy)propoxide (prepared as in Example 10) in 50 mL of benzonitrile at 25°. The reaction mixture warmed spontaneously to 40°. After stirring for one h at ambient temperature the more volatile portion of the reaction mixture was distilled out at reduced pressure, and then redistilled at atmospheric pressure to give 8.96 g (65%) of the ether as a colorless liquid: bp 64.4°; 1H NMR (CDCl3) δ3.71 ppm (s); 19F NMR (CDCl3) δ-54.1 ppm (m, 3F), -80.8 ppm (m, 3F), δ-88.6 ppm (m, 2F) and -146.1 ppm (m, 1F). Anal. Calcd. for C5H3F9O2 : C, 22.57; H, 1.14; F, 64.27. Found: C, 22.63; H, 1.17; F, 63.67.

Workup

  1. temperatureThe reaction mixture warmed spontaneously to 40°
  2. distillationwas distilled out at reduced pressure
  3. distillationredistilled at atmospheric pressure
  4. customto give 8.96 g (65%) of the ether as a colorless liquid

Sources & evidence

ORD record
ord-20e9556251ca4b899636249e6550b76b
Source dataset
uspto-grants-1986_11
Patent number
US04621125

Reaction notes

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