Reaktion #68523

Reaktionsgleichung

lithium bis(trimethylsilyl)amide

methyl 2-(quinolin-6-yl)acetate

methyl iodide

→

title compound

Ausbeute 85.0%

Methyl 2-(quinolin-6-yl)propanoate

Ausbeute 85.0%

Lösungsmittel

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThis was stirred for 30 min at −78° C.
2. 2
   Temperaturto warm to rt
3. 3
   SonstigeThe mixture was quenched with sat NH4Cl (40 mL)
4. 4
   workup.ADDITIONdiluted with water (200 mL)
5. 5
   EinengenThe mixture was concentrated in vacuo
6. 6
   Sonstigeto remove the THF
7. 7
   Extraktionwas extracted with EtOAc (2×100 ml)
8. 8
   WaschenThe combined extracts were washed with brine (50 ml)
9. 9
   Trocknendried (Na2SO4)
10. 10
    Einengenconcentrated onto silica
11. 11
    SonstigePurification by silica gel chromatography (20 to 60% EtOAc/hexane)

Vorschrift

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).

Quelle