Tetrahydrofuran → HCID 20086718, compound

HRID 2203106Notes

Reaction equation

HRID 2203106 reaction equation
[F:1][C:2]([F:10])([C:6]([F:9])([F:8])[F:7])[C:3]([NH2:5])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:20])=CC=1.C1COCC1.Br[CH2:39][C:40](=O)[C:41]([O:43][CH2:44][CH3:45])=[O:42]>O>[F:1][C:2]([F:10])([C:3]1[S:20][CH:39]=[C:40]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[N:5]=1)[C:6]([F:9])([F:8])[F:7]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 66144Ethyl bromopyruvateHCID 67722PerfluoropropanamideHCID 87949Lawesson's reagent

Product 1

HCID 20086718HCID 20086718, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,2,3,3,3-pentafluoropropanamide (2 g), Lawesson's reagent (2.98 g) and THF (30 ml) was heated under reflux overnight. Then ethyl 3-bromo-2-oxopropanoate (2.99 g) was added, and the mixture was heated at the same temperature overnight. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (0.91 g) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperaturethe mixture was heated at the same temperature overnight
  4. extractionextracted with EtOAc
  5. washThe extract was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. custompurified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-cdd61a25d1734672851349a5bfb6c020
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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