Indole → 1-Octyl-1H-indole

A solution of indole (1.0 g) in dry DMSO (1 ml) is dropped into a suspension of sodium hydride (60% suspension in mineral oil; 0.37 g) in dry DMSO (20 ml), heating to 60° C. for 1 h. After cooling at room temperature, the resulting solution is added dropwise with a solution of n-octyl bromide (2.82 ml) in dry DMSO (2.8 ml). After a night at room temperature, the reaction mixture is poured into water (200 ml) and extracted with ethyl acetate (2×50 ml). The combined organic phases are washed with a NaCl saturated solution, dried and evaporated to dryness. The resulting residue is purified by column chromatography (silica gel; eluent n-hexane) to obtain 1.86 g of 1-(n-octyl)indole as oil.

1. temperatureAfter cooling at room temperature
2. waitAfter a night at room temperature
3. extractionextracted with ethyl acetate (2×50 ml)
4. washThe combined organic phases are washed with a NaCl saturated solution
5. customdried
6. customevaporated to dryness
7. customThe resulting residue is purified by column chromatography (silica gel; eluent n-hexane)

ORD 기록

ord-047f1d28e35649159ae8b1dc2377d6b9

출처 데이터셋

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06987122B2