Pyridine → HCID 86597335, compound

HRID 2182193Notes

Reaction equation

HRID 2182193 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.C(N(CC)CC)C.[Cl-].[C:31]([O:38][CH2:39][CH:40]([CH2:45][CH3:46])[CH2:41][CH2:42][CH2:43][CH3:44])(=[O:37])/[CH:32]=[CH:33]\[C:34]([O-])=[O:35]>C(Cl)(Cl)Cl>[C:31]([O:38][CH2:39][CH:40]([CH2:45][CH3:46])[CH2:41][CH2:42][CH2:43][CH3:44])(=[O:37])/[CH:32]=[CH:33]\[C:34]([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:35]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 74883Fluorotelomer alcohol 4:2HCID 86590608HCID 86590608, compound

Product 1

HCID 86597335HCID 86597335, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3,3,4,4,5,5,6,6,6-Nonafluorohexanol (515 g, 1.95 mol), pyridine (169 g, 2.13 mol) and triethylamine (394 mL, 3.89 mol) were dissolved in chloroform (1000 mL) and added dropwise with 2-ethylhexyl maleate chloride (530 g, 2.14 mol), while the internal temperature was kept at 20° C. or lower on an ice bath. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour and then added with chloroform. The organic phase was washed with water 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 (508 g, yield: 50%), which was colorless and transparent.

Workup

  1. customwas kept at 20° C. or lower on an ice bath
  2. additionAfter completion of the addition
  3. washThe organic phase was washed with water
  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-654e3e77056f4150a3da9dd3f3d9a81c
Source dataset
uspto-grants-2005_05
Patent number
US06897013B2

Reaction notes

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