Trifluoromethanesulfonic anhydride → Ethanethioic acid trans(+/-)-S-[tetrahydro-5-[[[(trifluoromethyl)sulfonyl]oxy]methyl]-3-furanyl]ester

HRID 1290354Notes

Reaction equation

HRID 1290354 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.O[CH2:17][C@@H:18]1[O:22][CH2:21][C@@H:20]([S:23][C:24](=[O:26])[CH3:25])[CH2:19]1>C(Cl)Cl.N1C=CC=CC=1>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][CH2:17][C@@H:18]1[O:22][CH2:21][C@@H:20]([S:23][C:24](=[O:26])[CH3:25])[CH2:19]1)(=[O:8])=[O:9]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 15346553Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-(hydroxymethyl)-3-furanyl]ester

Product 1

HCID 86750748Ethanethioic acid trans(+/-)-S-[tetrahydro-5-[[[(trifluoromethyl)sulfonyl]oxy]methyl]-3-furanyl]ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 0.535 ml of trifluoromethanesulfonic anhydride in 3.75 ml of methylene chloride is added, via a syringe, a 0° C. solution of 0.529 g of product from Example 6 in 0.75 ml of methylene chloride and 0.243 ml of pyridine. The reaction is stirred in an ice bath for 45 minutes; during which time the progress of reaction is checked by thin layer chromatography. The mixture is concentrated in vacuo, slurried with ethyl acetate and filtered. The filtrate is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane) to give 0.799 g of the desired product.

Workup

  1. customduring which time the progress of reaction
  2. concentrationThe mixture is concentrated in vacuo
  3. filtrationfiltered
  4. customThe filtrate is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f22d5f2a852f4fc0b8463158c9f63e9b
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

Loading…