反应详情

Cool a solution of methyl lithium in ether (200 mL, 1.6 M, 320.00 mmol) in an ice bath and add 4-tert-butyl-pyridine (20.28 g, 150.00 mmol) drop wise. Once the substrate is added, warm the reaction to ambient temperature for 3 hours. Concentrate the reaction to near dryness to remove the ether and then add anhydrous toluene (200 mL) and heat to reflux for 20-21 hours. Cool in an ice bath while slowly and cautiously adding ice to quench the reaction. Add water (200 mL) and then extract the aqueous with ethyl acetate (3×250 mL) and separate the layers. Pool, desiccate, filter and concentrate the organic extracts to an oil. Chromatograph the oil on silica using a gradient of 0→50% ethyl acetate hexanes over 25 minutes to yield the title compound (16.60 g, 111.23 mmol). MS(ESI), m/z 150 (M+1).

1. additionOnce the substrate is added
2. temperaturewarm
3. customthe reaction to ambient temperature for 3 hours
4. concentrationConcentrate
5. customthe reaction
6. customto remove the ether
7. temperatureadd anhydrous toluene (200 mL) and heat
8. temperatureto reflux for 20-21 hours
9. temperatureCool in an ice bath while slowly and cautiously adding ice
10. customto quench
11. customthe reaction
12. extractionAdd water (200 mL) and then extract the aqueous with ethyl acetate (3×250 mL)
13. customseparate the layers
14. filtrationPool, desiccate, filter
15. concentrationconcentrate the organic extracts to an oil