Perfluorobutyl iodide → 1-(2-Methyl-1,3-dioxolan-2-yl)-alpha-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)cyclopropanemethanol

HRID 842622Notes

Reaction equation

HRID 842622 reaction equation
[CH3:1][C:2]1([C:7]2([CH:10]=[O:11])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4][O:3]1.[F:12][C:13](I)([F:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17].C[Li].[Br-].[Li+]>C(OCC)C>[CH3:1][C:2]1([C:7]2([CH:10]([C:13]([F:24])([F:12])[C:14]([F:22])([F:23])[C:15]([F:20])([F:21])[C:16]([F:19])([F:18])[F:17])[OH:11])[CH2:9][CH2:8]2)[O:3][CH2:4][CH2:5][O:6]1

Participants

5

Reactant 3

HCID 67917Perfluorobutyl iodideHCID 143755571-(2-Methyl-1,3-dioxolan-2-YL)cyclopropane-1-carbaldehydeHCID 178419607HCID 178419607, compound

Product 1

HCID 226144181-(2-Methyl-1,3-dioxolan-2-yl)-alpha-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)cyclopropanemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.2 g of 97 and 3.92 ml of perfluorobutyl iodide in 40 ml of diethyl ether are introduced under argon and methyllithium/lithium bromide complex (1.5 M in diethyl ether) is added in drops at −78° C. After 30 minutes, it is quenched with sodium chloride solution and diluted with ethyl acetate. Extraction with ethyl acetate, washing of the combined organic phases with sodium chloride solution, drying on sodium sulfate, removal of the solvent and chromatography on silica gel with ethyl acetate/hexane yields 2.1 g of 1-(2-methyl-1,3-dioxolan-2-yl)-α-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)cyclopropanemethanol 98 as a colorless oil.

Workup

  1. customit is quenched with sodium chloride solution
  2. additiondiluted with ethyl acetate
  3. extractionExtraction with ethyl acetate
  4. washwashing of the combined organic phases with sodium chloride solution
  5. dry with materialdrying on sodium sulfate, removal of the solvent and chromatography on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-42402f6f06fa421ea9fddd945be55418
Source dataset
uspto-grants-2002_04
Patent number
US06376480B1

Reaction notes

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