Pyridine → HCID 86597333, compound

HRID 2182192Notes

Reaction equation

HRID 2182192 reaction equation
[F:1][C:2]([F:16])([C:6]([F:15])([F:14])[C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])[CH2:3][CH2:4][OH:5].N1C=CC=CC=1.[Cl-].[C:24]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]CC)(=[O:30])/[CH:25]=[CH:26]\[C:27]([O-])=[O:28].C(OCC)(=O)C>C(Cl)(Cl)Cl>[C:24]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])(=[O:30])/[CH:25]=[CH:26]\[C:27]([O:5][CH2:4][CH2:3][C:2]([F:16])([F:1])[C:6]([F:14])([F:15])[C:7]([F:12])([F:13])[C:8]([F:9])([F:10])[F:11])=[O:28]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 74883Fluorotelomer alcohol 4:2HCID 86759731HCID 86759731, compound

Product 1

HCID 86597333HCID 86597333, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3,3,4,4,5,5,6,6,6-Nonafluorohexanol (164.6 g, 623 mmol) and pyridine (49.3 mL, 623 mmol) were dissolved in chloroform (280 mL), and the mixture was added dropwise with monododecyl maleate chloride (155.8 g, 566 mmol), while the internal temperature was kept at 20° C. or lower on an ice bath. After completion or the addition, the mixture was stirred for 1 hour and added with ethyl acetate. 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 (48.2 g, yield: 18%).

Workup

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

Sources & evidence

ORD record
ord-fa97ed03c95a4762b2eef0855df6058c
Source dataset
uspto-grants-2005_05
Patent number
US06897013B2

Reaction notes

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