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温度

0 °C

A solution of methyl p-aminobenzoate (0.45 g, 3.0 mmole) in 6 mL tetrahydrofuran (THF) was cooled to −78° C. and treated dropwise with 2.5 M n-butyllithium solution (1.32 mL). The reaction mixture was allowed to warm to 0° C. over a one hour period. Iodopentane (0.78 mL) was introduced at −40° C. and the mixture was stirred at room temperature for 15 hours. The reaction mixture was poured into 50 mL of a saturated aqueous sodium bicarbonate solution and extracted with three portions of 50 mL of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, giving a brown oil. The product was purified by flash chromatography (SiO2, 10%-20% ethyl acetate/hexanes) to provide 140 mg (23%) of methyl 4-pentylaminobenzoate (43) as a pale yellow oil.

1. extractionextracted with three portions of 50 mL of ether
2. dry with materialThe combined organic extracts were dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customgiving a brown oil
6. customThe product was purified by flash chromatography (SiO2, 10%-20% ethyl acetate/hexanes)