Methyl 4-aminobenzoate → Methyl 4-pentylaminobenzoate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence