Pyridine → HCID 86597336, compound

HRID 2182194Notes

Reaction equation

HRID 2182194 reaction equation
[F:1][C:2]([F:10])([F:9])[CH:3]([OH:8])[C:4]([F:7])([F:6])[F:5].N1C=CC=CC=1.[Cl-].[C:18]([O:25][CH2:26][CH:27]([CH2:32][CH3:33])[CH2:28][CH2:29][CH2:30][CH3:31])(=[O:24])/[CH:19]=[CH:20]\[C:21]([O-])=[O:22].C(OCC)(=O)C>C(#N)C>[C:18]([O:25][CH2:26][CH:27]([CH2:32][CH3:33])[CH2:28][CH2:29][CH2:30][CH3:31])(=[O:24])/[CH:19]=[CH:20]\[C:21]([O:8][CH:3]([C:4]([F:7])([F:6])[F:5])[C:2]([F:10])([F:9])[F:1])=[O:22]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 86590608HCID 86590608, compound

Product 1

HCID 86597336HCID 86597336, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP, 33.7 g, 201 mmol) and pyridine (17.9 mL, 220 mmol) were dissolved in acetonitrile (80 mL) and added dropwise with mono(2-ethylhexyl) maleate chloride (41.8 g, 220 mmol), while the internal temperature was kept at 20° C. or lower by cooling the solution on an ice bath. After completion of the addition, the reaction mixture was stirred at room temperature for 1hour and added with ethyl acetate, and the organic phase was washed with 1 mol/L aqueous hydrochloric acid and a saturated sodium chloride aqueous solution. Then, the organic layer was collected, and the organic solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/chloroform=10/0 to 7/3 (v/v)) to obtain the target compound (10.6 g, yield: 14%) as a colorless transparent oily compound.

Workup

  1. customwas kept at 20° C.
  2. temperaturelower by cooling the solution on an ice bath
  3. additionAfter completion of the addition
  4. washthe organic phase was washed with 1 mol/L aqueous hydrochloric acid
  5. customThen, the organic layer was collected
  6. customthe organic solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/chloroform=10/0 to 7/3 (v/v))

Sources & evidence

ORD record
ord-acda8d82c71d430eaa3d76ca26d8251d
Source dataset
uspto-grants-2005_05
Patent number
US06897013B2

Reaction notes

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