Pyridine → (S)-Glycidyl triflate

HRID 280366Notes

Reaction equation

HRID 280366 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].[CH2:22]1[O:24][C@@H:23]1[CH2:25]O.CCCCCC>C(Cl)Cl>[O:12]([CH2:25][C@H:23]1[O:24][CH2:22]1)[S:9]([C:8]([F:21])([F:20])[F:7])(=[O:10])=[O:11]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8058HexaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 5460455(+)-Glycidol

Product 1

HCID 11063586(S)-Glycidyl triflateYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To pyridine (10.3 g, 0.13 m) in CH2Cl2 (300 ml) cooled to -23° in a dry ice/CCl4 bath was added trifluoromethanesulfonic anhydride (36.7 g, 0.13 m) in CH2Cl2 (100 ml) dropwise over 1/2 hour. While still cooling this mixture at -23°, (R)-glycidol (8.6 g, 0.116 m) in CH2Cl2 (100 ml) was added dropwise over 1/2 hour. After stirring for 5 minutes with cooling and 15 minutes without, an equal volume of hexane was added and the solids were filtered. Concentration of the solution at 30°/25 torr. left a residue which was distilled to give (S)-3-trifloxy-1,2-epoxypropane (40%); bp 35°-39°/0.2 mm; [α]D24 =14.7° (c=3.90, CHCl3); 1H NMR (CDCl3) 4.8 (1H, d of d, J=11, J=3 ), 4.4 (1H, d of d, J=11, J=3), 3.3 (1H, m), 2.9 (1H, t, J=4.5), 2.7 (1H, J=4.5, J=2).

Workup

  1. temperatureWhile still cooling this mixture at -23°
  2. additionwas added
  3. filtrationthe solids were filtered
  4. customat 30°
  5. waitleft a residue which
  6. distillationwas distilled

Sources & evidence

ORD record
ord-9b114507a2924e58ae917e4e7aca2efe
Source dataset
uspto-grants-1986_05
Patent number
US04588824

Reaction notes

Loading…