Benzene → HCID 86734703, compound

HRID 329308Notes

Reaction equation

HRID 329308 reaction equation
Cl[C@:2]1([O:9][C@@H:8]([CH3:10])[C@@:6]([O:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])([OH:7])[C@@H:5]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:4]1)O.C1C=CC=CC=1.[Hg](C#N)C#N>O1CCOCC1>[F:23][C:20]([F:21])([F:22])[C:19]([NH:18][C@@H:5]1[C@:6]([O:11][C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])([OH:7])[C@H:8]([CH3:10])[O:9][CH:2]=[CH:4]1)=[O:24]

Participants

5

Reactant 3

HCID 241BenzeneHCID 11591Mercuric cyanideHCID 86734704HCID 86734704, compound

Product 1

HCID 86734703HCID 86734703, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 800 mg of 1-chloro-2,3,6-trideoxy-3-trifluoroacetamido-4-trifluoroacetoxy-alpha-L-lyxohexopyranose (I)* in 25 ml of a 4:1 (by volume) mixture of benzene and dioxane there were added 500 mg of Hg(CN)2. The resulting suspension was heated under reflux for 3 1/2 hours. After cooling, the reaction mixture was filtered to give a clear solution, which was then evaporated to a residue. The residue was extracted with benzene and, upon evaporation of the benzene solution, there were obtained 650 mg of 1,2,3,6-tetradeoxy-3-trifluoroacetamido-4-trifluoroacetoxy-L-lyxo-hex-1-enopyranose (II) in crystalline form melting at 73°-74° C.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureunder reflux for 3 1/2 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. customto give a clear solution, which
  6. customwas then evaporated to a residue
  7. extractionThe residue was extracted with benzene and, upon evaporation of the benzene solution

Sources & evidence

ORD record
ord-83cfafdd838947c0bafe21053ae78918
Source dataset
uspto-grants-1977_04
Patent number
US04020270

Reaction notes

Loading…