Tetrahydrofuran → HCID 18953814, compound

HRID 2379811Notes

Reaction equation

HRID 2379811 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[C:12](C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:13].O1CCC[CH2:35]1>>[C:10]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:1]=[CH:2]/[C:12]#[N:13])[N:9]=1)(=[O:11])[CH3:35]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 189538106-Acetylpyridine-2-carbaldehyde

Product 1

HCID 18953814HCID 18953814, compound

Procedure

A mixture of 6-acetyl-2-pyridinecarbaldehyde (0.5 g) and cyanomethylenetriphenylphosphorane (1.5 g) in tetrahydrofuran (5 ml) was stirred for 6 hours and the mixture was evaporated in vacuo. The residue was separated and purified by column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate (4:1, V/V). The eluted fast fractions containing the desired product were collected and evaporated in vacuo to give 2-acetyl-6-[2-(E)-cyanovinyl]pyridine (0.18 g).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customThe residue was separated
  3. custompurified by column chromatography on silica gel
  4. washeluted with a mixture of n-hexane and ethyl acetate (4:1, V/V)
  5. washThe eluted fast fractions
  6. additioncontaining the desired product
  7. customwere collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-303292326b40429988c90d5c9786317a
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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