Pyridine → HCID 86628935, compound

HRID 2236119Notes

Reaction equation

HRID 2236119 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].N1C=CC=CC=1.O[C@H:23]1[CH2:28][CH2:27][O:26][C:24]1=[O:25]>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C@H:23]1[CH2:28][CH2:27][O:26][C:24]1=[O:25])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 3578532-Hydroxy-gamma-butyrolactone, (2S)-

Product 1

HCID 86628935HCID 86628935, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (1.65 mL) was gently added to a solution of pyridine (0.83 mL) in dichloromethane mL) at 0° C., and the mixture was stirred for 5 minutes at the same temperature. Subsequently, (S)-2-hydroxybutyrolactone (1.0 g) was added dropwise thereto over 10 minutes at 0° C., followed by stirring for 12 hours at the same temperature. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=2/1), to thereby yield a colorless oil (1.40 g, 61.2%).

Workup

  1. waitover 10 minutes at 0° C.
  2. stirringby stirring for 12 hours at the same temperature
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-2d09dd5bf4934befbf75e525042e1bf5
Source dataset
uspto-grants-2010_05
Patent number
US07714141B2

Reaction notes

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