Methyl triflate → HCID 13765569, compound

HRID 1731404Notes

Reaction equation

HRID 1731404 reaction equation
F[C:2](F)(F)S(OC)(=O)=O.[F:10][C:11]([F:30])([C:13]([F:29])([O:18][C:19]([F:28])([F:27])[C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[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:30])[C:13]([F:29])([O:18][C:19]([F:27])([F:28])[C:20]([F:26])([F:25])[C:21]([F:22])([F:24])[F:23])[C:14]([F:17])([F:16])[F:15]

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 20225811HCID 20225811, compound

Product 1

HCID 13765569HCID 13765569, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 7505BenzonitrileSolvent

Procedure

Methyl trifluoromethanesulfonate, 4.92 g (0.03 mol), was added dropwise to 0.03 mol of tris(dimethylamino)sulfonium 1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propoxide (prepared as in Example 13) in 30 mL of benzonitrile. The reaction mixture was stirred for 1.5 h and then the more volatile portion of the reaction mixture was distilled out at reduced pressure and redistilled at atmospheric pressure to give 6.39 g (58%) of methyl 1,1,2,3,3,3-hexafluoro-2-(heptafluoropropoxy)propyl ether as a colorless liquid: bp 94°-96°; 1H NMR (CDCl3) δ3.70 ppm (s); 19F NMR (CD3Cl) δ-81.0 ppm (m, 3F), -82.1 ppm (m, 3F), -82.4 ppm (m, 2F), -88.7 ppm (m, 2F), -130.3 ppm (m, 2F) and -144.8 ppm (m, 1F). Anal. Calcd. for C7H3F13O2 : C, 22.96; H, 0.82. Found: C, 22.95; H, 0.78.

Workup

  1. distillationthe more volatile portion of the reaction mixture was distilled out at reduced pressure
  2. distillationredistilled at atmospheric pressure

Sources & evidence

ORD record
ord-2ab243319cef4caca697b0a0e6225a3f
Source dataset
uspto-grants-1986_11
Patent number
US04621125

Reaction notes

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