Triphenylphosphine Oxide → (E)-Methyl 3-[3-(phenylmethoxy)pyridin-2-yl]-2-propenoate

HRID 1088716Notes

Reaction equation

HRID 1088716 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:10]([CH:15]=O)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH3:20])=[O:18].C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[C:1]1([CH2:7][O:8][C:9]2[C:10](/[CH:15]=[CH:21]/[C:17]([O:19][CH3:20])=[O:18])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 133745943-(Benzyloxy)pyridine-2-carbaldehyde

Product 1

HCID 22161738(E)-Methyl 3-[3-(phenylmethoxy)pyridin-2-yl]-2-propenoateYield 712.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Crude 3-(phenylmethoxy)-2-pyridinecarboxaldehyde (30 g) and carbomethoxymethylenetriphenylphosphorane (55 g) in acetonitrile (800 ml) were stirred at reflux overnight. The solution was evaporated onto silica (Merck 9385) which was then purified by FCC eluting with ethyl acetate to give the product contaminated with triphenylphosphine oxide. This crude product was triturated with ether and the triturate was evaporated to an oil which was chromatographed on a column of silica (Merck 9385) eluting with cyclohexane followed by cyclohexane/ethyl acetate (4:1) to give the title compound as a yellow oil (270 g), t.l.c. (cyclohexane/ethyl acetate/triethylamine 80:20:1) Rf 0.17.

Workup

  1. temperatureat reflux overnight
  2. customThe solution was evaporated onto silica (Merck 9385) which
  3. customwas then purified by FCC
  4. washeluting with ethyl acetate
  5. customto give the product
  6. customThis crude product was triturated with ether
  7. customthe triturate was evaporated to an oil which
  8. customwas chromatographed on a column of silica (Merck 9385)
  9. washeluting with cyclohexane

Sources & evidence

ORD record
ord-b19d30b2c97b4997ae5e7c54a3008a08
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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