substitution mechanism. A study of the mechanism of this reaction is underway and will be communicated in a later
publication.
Acknowledgment
This research was supported by funding from the Ball State University Provost’s start-up funds and the Ball State
University Department of Chemistry.
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20. Procedure for the synthesis of 2. A 3-necked, 500 mL, round-bottomed flask was equipped with stir bar, reflux condenser fitted with a N2 inlet
adapter, and 2 glass stoppers. Allyl alcohol (5.80 mL, 88.1 mmol), followed by 2-chloropyridine (5.00 mL, 52.7 mmol), and toluene (105 ml) were
added sequentially to the flask. Potassium hydroxide (85%, 12.0g, 176 mmol) was ground in a mortar in pestle, then added to the reaction flask
followed by 18-crown-6 (0.278 g, 1.04 mmol). The reaction mixture was heated at reflux (oil bath at 115 °C) for 2h. After cooling to room
temperature, the reaction mixture was diluted with diethyl ether (150 mL), washed with water (1 x 50 mL), followed by brine (1 x 50 mL). The
organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo to a pale yellow liquid. Column chromatography of the residue
(29:1 hexanes/ethyl acetate) yielded the product as a pale yellow oil (6.73 g, 49.8 mmol, 95%).
21. General procedure for the formation of allyl esters: A 5-mL reaction vial was equipped with a stir bar, a rubber septum, and an argon inlet
needle. The vial was charged with allyloxypyridine (2) (1.1 equiv), carboxylic acid (4) (1.0 equiv), and dry PhCH3 (2.5 mL), and was allowed
to stir at 0 °C. MeOTf (1.1 equiv) was added dropwise to the reaction mixture over 2 min. Upon complete addition, the ice bath was removed
and the reaction was allowed to stir for 1h or until 2 was completely consumed as indicated by TLC. The septum was quickly replaced with a
reflux condenser fitted with an N2 inlet adapter. The reaction mixture was heated at reflux (oil bath 115 °C), and K2CO3 (0.95 equiv) was
added in one portion through the top of the reflux condenser. Upon complete consumption of the carboxylic acid as indicated by TLC
typically (1-2h), the mixture was diluted with ethyl acetate (10 mL). The diluted reaction mixture was washed with water (1 x 10 mL),
followed by brine (1 x 10 mL). The organic fraction was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to isolate
the crude product mixture. The crude mixture was purified by flash chromatography to yield the allyl ester product (5).