Реакция #68523

Уравнение реакции

lithium bis(trimethylsilyl)amide

methyl 2-(quinolin-6-yl)acetate

methyl iodide

→

title compound

Выход 85.0%

Methyl 2-(quinolin-6-yl)propanoate

Выход 85.0%

Растворители

tetrahydrofuran

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGThis was stirred for 30 min at −78° C.
2. 2
   Температураto warm to rt
3. 3
   ДругоеThe mixture was quenched with sat NH4Cl (40 mL)
4. 4
   workup.ADDITIONdiluted with water (200 mL)
5. 5
   КонцентрированиеThe mixture was concentrated in vacuo
6. 6
   Другоеto remove the THF
7. 7
   Экстракцияwas extracted with EtOAc (2×100 ml)
8. 8
   ПромывкаThe combined extracts were washed with brine (50 ml)
9. 9
   Сушкаdried (Na2SO4)
10. 10
    Концентрированиеconcentrated onto silica
11. 11
    ДругоеPurification by silica gel chromatography (20 to 60% EtOAc/hexane)

Методика

To a 250 ml round-bottomed flask was added lithium bis(trimethylsilyl)amide (2.0 g, 12 mmol) and tetrahydrofuran (75 ml). The mixture was cooled to −78° C. and methyl 2-(quinolin-6-yl)acetate (2.0 g, 9.9 mmol) was added as a solution in 1 ml THF. This was stirred at −78° C. for 30 min and then methyl iodide (0.75 ml, 12 mmol) was added. This was stirred for 30 min at −78° C. and then allowed to warm to rt. The mixture was quenched with sat NH4Cl (40 mL) and diluted with water (200 mL). The mixture was concentrated in vacuo to remove the THF and then was extracted with EtOAc (2×100 ml). The combined extracts were washed with brine (50 ml), dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (20 to 60% EtOAc/hexane) afforded the title compound as a brown oil (1.8 g, 85%). MS (ESI, pos. ion) m/z: 216 (M+1).

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