Toluene → 5-(Benzyloxy)-2-vinylpyridine

Participants

Reaction Steps

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).

Provenance & Evidence