Water → 2-(2,2,2-Trifluoroethoxy)-5-vinylpyridine

HRID 623475Notes

Reaction equation

HRID 623475 reaction equation
[CH2:1]([Li])CCC.[F:6][C:7]([F:19])([F:18])[CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][N:11]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[F:6][C:7]([F:19])([F:18])[CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[CH2:1])=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 216984996-(2,2,2-Trifluoroethoxy)nicotinaldehydeHCID 178418339Butyllithium

Product 1

HCID 675114252-(2,2,2-Trifluoroethoxy)-5-vinylpyridineYield 75%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (5.14 mL, 13.4 mmol) is added to a suspension of methyltriphenylphosphonium bromide (4.41 g, 12.34 mmol) in tetrahydrofuran (51 mL) at −78° C. under nitrogen atmosphere. The reaction mixture is warmed to room temperature to yield deep red ylide solution. To ylide solution, cooling in ice, is introduced 6-(2,2,2-trifluoroethoxy)nicotinaldehyde (2.11 g, 10.3 mmol, Step-1) in tetrahydrofuran (10 mL) and stirred at room temperature for 3 hours. The reaction mixture is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (10:1) to give 1.56 g (75% yield) of the title compound as colorless oil.

Workup

  1. customto yield deep red ylide solution
  2. temperaturecooling in ice
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-5f0cc23d162b40d080072868af2cd49a
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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