Triphenylphosphine → Methyl 6-[1-(3-pyridyl)ethenyl]-2-naphthoate

HRID 569796Notes

Reaction equation

HRID 569796 reaction equation
O[C:2]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=[CH:13]2)([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClC(Cl)(Cl)Cl>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:2]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=[CH:13]3)=[CH2:3])[CH:5]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 13687913HCID 13687913, compound

Product 1

HCID 20146227Methyl 6-[1-(3-pyridyl)ethenyl]-2-naphthoateYield 86.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

0.3 g (1 mmol) of methyl 6-[1-hydroxy-1-(3-pyridyl)ethyl]-2-naphthoate and 0.68 g (2.6 mmol) of triphenylphosphine in 3 ml of tetrachloromethane are heated under reflux for 9 hours. After evaporation, the residue is taken up in 4 N HCL, and triphenylphosphine and triphenylphosphine oxide are extracted with ethyl acetate. The aqueous phase is then neutralized with sodium bicarbonate. After extraction with ethyl acetate, and drying and evaporation of the ethyl acetate phase in vacuo, 0.25 g (86%) of methyl 6-[1-(3-pyridyl)ethenyl]-2-naphthoate is obtained as an oil. RF (ethyl acetate/methanol 8:1): 0.59. 1H-NMR (CDCl3, 60 MHz) δ=4.0 (2, 3H; CH3), 5.7 (d, 2H; C=CH2), 7.0-8.7 (m, 10H; arom. H).

Workup

  1. temperatureunder reflux for 9 hours
  2. customAfter evaporation
  3. extractionare extracted with ethyl acetate
  4. extractionAfter extraction with ethyl acetate
  5. customdrying
  6. customevaporation of the ethyl acetate phase in vacuo

Sources & evidence

ORD record
ord-c65ccc8949514170bef68af4db87a308
Source dataset
uspto-grants-1988_03
Patent number
US04734406

Reaction notes

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