Toluene → 5-(Benzyloxy)-2-vinylpyridine

HRID 1249622Notes

Reaction equation

HRID 1249622 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=O)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:19]1(C)C=CC=CC=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[CH2:19])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 123972545-(Benzyloxy)pyridine-2-carbaldehyde

Product 1

HCID 133401705-(Benzyloxy)-2-vinylpyridine

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

In a two liter 3-neck round bottom flask fitted with a mechanical stirrer, thermometer and a watercooled reflux condenser was placed 23.4 g. (0.11 mole) of 5-benzyloxypyridine-2-carbaldehyde, 78.5 g. (0.22 mole) of methyltriphenylphosphonium bromide and 26.5 g. (0.66 mole) of sodium hydroxide pellets in 250 ml. of toluene and 665 ml. of water. The reaction mixture was stirred at room temperature for 15 hours. The toluene layer was separated and saved. The aqueous layer was washed with toluene and the combined toluene layers are filtered through a 4"×641 pad of silica gel to remove triphenylphosphate. The pad was successively washed with toluene, then ether/hexane (3:2) to remove the desired product. The organic solutions were combined, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to give 5-benzyloxy-2-vinylpyridine as a yellow oil (20.5 g., 73.7%); NMR (CDCl3) 8.15 (m, 1H, H6), 7.16 (s, 5H, C6H 5 -), 7.00 (m, 2H, H3 and H4), 6.67 (d of d, 1H, oletin H), 5.95 (d of d, 1H, oletin H), 5.15 (d of d, 1H, oletin H) and 4.90 (3, 2H, CH2).

Workup

  1. customIn a two liter 3-neck round bottom flask fitted with a mechanical stirrer
  2. customthermometer and a watercooled reflux condenser was placed
  3. customThe toluene layer was separated
  4. washThe aqueous layer was washed with toluene
  5. filtrationthe combined toluene layers are filtered through a 4"×641 pad of silica gel
  6. customto remove triphenylphosphate
  7. washThe pad was successively washed with toluene
  8. customether/hexane (3:2) to remove the desired product
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb66cc7f173142e9b437ae801e1ee010
Source dataset
uspto-grants-1986_12
Patent number
US04632992

Reaction notes

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