反応 #68523

反応方程式

lithium bis(trimethylsilyl)amide

methyl 2-(quinolin-6-yl)acetate

methyl iodide

→

title compound

収率 85.0%

Methyl 2-(quinolin-6-yl)propanoate

収率 85.0%

溶媒

tetrahydrofuran

THF

反応条件

後処理

1. 1
   workup.STIRRINGThis was stirred for 30 min at −78° C.
2. 2
   温度to warm to rt
3. 3
   その他The mixture was quenched with sat NH4Cl (40 mL)
4. 4
   workup.ADDITIONdiluted with water (200 mL)
5. 5
   濃縮The mixture was concentrated in vacuo
6. 6
   その他to remove the THF
7. 7
   抽出was extracted with EtOAc (2×100 ml)
8. 8
   洗浄The combined extracts were washed with brine (50 ml)
9. 9
   乾燥dried (Na2SO4)
10. 10
    濃縮concentrated onto silica
11. 11
    その他Purification by silica gel chromatography (20 to 60% EtOAc/hexane)

実験手順

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).

出典