Hexane → HCID 19422277, compound

HRID 2254404Notes

Reaction equation

HRID 2254404 reaction equation
[Cl-].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH:34](=O)[C:35]1[CH:42]=[CH:41][CH:40]=[C:37]([CH:38]=[O:39])[CH:36]=1.CCCCCC>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH:38]([C:37]1[CH:36]=[C:35](/[CH:34]=[CH:8]/[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:42]=[CH:41][CH:40]=1)=[O:39]

Participants

7

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 34777IsophthalaldehydeHCID 11058219Phosphonium, triphenyl(2-pyridinylmethyl)-, chloride

Product 1

HCID 19422277HCID 19422277, compoundYield 374.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

3.9 g of (2-pyridyl)methyltriphenylphosphonium chloride was suspended in 20 ml of tetrahydrofuran, and with stirring, 5.3 ml of a 20% aqueous solution of potassium carbonate and 0.13 g of isophthalaldehyde were added. The mixture was stirred overnight at room temperature. Hexane was added, and the resulting aqueous layer was discarded, and concentrated under reduced pressure. Hexane was added to the residue. The insoluble matter was removed by filtration, and the filtrate was evaporated under reduced pressure. The residue was purified by medium-pressure liquid chromatography [column: Lobar column, size B, Lichroprep Si 60 (a product of E. Merck Co.); eluting solvent: hexane/ethyl acetate=7/1→4/1]to give 0.76 g (yield 36%) of (E)-2-[2-(3-formylphenyl)vinyl]pyridine.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionHexane was added to the residue
  4. customThe insoluble matter was removed by filtration
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by medium-pressure liquid chromatography [column

Sources & evidence

ORD record
ord-f3327b710d0a493881946a973bf0baad
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

Loading…