Pyridine → HCID 58623337, compound

HRID 1296859Notes

Reaction equation

HRID 1296859 reaction equation
[F:1][C:2]([F:34])([F:33])[CH:3]([O:5][CH2:6][CH2:7][C:8]([F:32])([F:31])[C:9]([F:30])([F:29])[C:10]([F:28])([F:27])[C:11]([F:26])([F:25])[C:12]([F:24])([F:23])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])O.S(Cl)([Cl:37])=O.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:37][CH:3]([O:5][CH2:6][CH2:7][C:8]([F:32])([F:31])[C:9]([F:30])([F:29])[C:10]([F:28])([F:27])[C:11]([F:26])([F:25])[C:12]([F:24])([F:23])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[C:2]([F:34])([F:33])[F:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 58623364HCID 58623364, compound

Product 1

HCID 58623337HCID 58623337, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 1.0 M hexane solution (34 ml) of diisobutylaluminum hydride (hereinafter, referred to as DIBAL) was added, dropwise, at −70° C., to a tetrahydrofuran solution (60 ml) of 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl trifluoroacetate ester (18.3 g) obtained by reaction of trifluoroacetic anhydride and 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecanol, followed by stirring at −70 to −50° C. for 2 hours. The resultant reaction solution was allowed to warm gradually to 0° C., and 1-mol/L aqueous hydrochloric acid (5 ml) was added thereto, followed by stirring at the same temperature for 5 minutes. After extraction with ethyl acetate/1 mol/L-hydrochloric acid, the organic layer was washed with water and an aqueous sodium chloride solution, and then dried over magnesium sulfate. The solvent was concentrated under reduced pressure, to give crude 2,2,2-trifluoro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyloxy)ethanol. The resultant crude alcohol was dispersed in toluene (50 ml), and thionyl chloride (3.5 ml) and pyridine (4.0 ml) were added thereto, dropwise, at room temperature, followed by stirring for 3 hours. After the reaction solution was extracted with ethyl acetate/1 mol/L-aqueous hydrochloric acid, the organic layer was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The concentrated residue was purified by column chromatography (developing solvent: ethyl acetate/hexane=1/9), to give 10-(1-chloro-2,2,2-trifluoroethoxy)-1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluorodecane (11.9 g, 63%).

Workup

  1. customat room temperature
  2. extractionAfter the reaction solution was extracted with ethyl acetate/1 mol/L-aqueous hydrochloric acid
  3. washthe organic layer was washed with water
  4. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrated residue was purified by column chromatography (developing solvent: ethyl acetate/hexane=1/9)

Sources & evidence

ORD record
ord-1d0da1649d8546ac8ea1ad8265538e08
Source dataset
uspto-grants-2007_07
Patent number
US07247757B2

Reaction notes

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