4-Pyridinecarboxaldehyde → HCID 14461436, compound

HRID 2352350Notes

Reaction equation

HRID 2352350 reaction equation
[Br-].[CH3:2][C:3]1([CH3:36])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7]([CH:15]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:16])[CH:6]=[CH:5][C:4]1=2.[N:37]1[CH:42]=[CH:41][C:40]([CH:43]=O)=[CH:39][CH:38]=1>C1OCCC1>[CH3:2][C:3]1([CH3:36])[CH2:12][CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2[CH:8]=[C:7](/[C:15](/[CH3:16])=[CH:43]/[C:40]3[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=3)[CH:6]=[CH:5][C:4]1=2

Participants

4

Reactant 2

HCID 133894-PyridinecarboxaldehydeHCID 11238302Triphenyl(1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethyl)phosphonium bromide

Product 1

HCID 14461436HCID 14461436, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

378 g of [1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethyl]triphenylphosphonium bromide were suspended in 4 l of butylene oxide. After the addition of 51 ml of 4-pyridinecarbaldehyde the mixture was boiled at reflux for 1.5 hours. After cooling the majority of the solvent was evaporated in a water-jet vacuum, the residue was poured into 1.5 l of a methanol/water mixture (ratio 6:4) and extracted repeatedly with hexane. The organic phase was washed three times with water and, after drying over sodium sulphate, evaporated. After flash chromatography (eluting agent hexane/ether=2:1) and recrystallization from hexane there were obtained 216 g of 4-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)propenyl]pyridine in colorless crystals, melting point 84°-85°.

Workup

  1. temperatureat reflux for 1.5 hours
  2. temperatureAfter cooling the majority of the solvent
  3. customwas evaporated in a water-jet vacuum
  4. additionthe residue was poured into 1.5 l of a methanol/water mixture (ratio 6:4)
  5. extractionextracted repeatedly with hexane
  6. washThe organic phase was washed three times with water
  7. dry with materialafter drying over sodium sulphate
  8. customevaporated
  9. washAfter flash chromatography (eluting agent hexane/ether=2:1) and recrystallization from hexane

Sources & evidence

ORD record
ord-3fd8baa4aedb41d2a69c8cc796de90a1
Source dataset
uspto-grants-1989_10
Patent number
US04876349

Reaction notes

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