Reaktion #68526

Reaktionsgleichung

methyl 2-(quinolin-6-yl)acetate

n-fluorobenzenesulfonimide

lithium bis(trimethylsilyl)amide

→

title compound

Methyl 2-fluoro-2-(quinolin-6-yl)acetate

Lösungsmittel

THF

THF

tetrahydrofuran

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 (50 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 (100 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. After stirring at −78° C. for 30 min, n-fluorobenzenesulfonimide (3.8 g, 12 mmol) was added as a 1 M solution in THF. This was stirred for 30 min at −78° C. and then allowed to warm to rt. The mixture was quenched with sat NH4Cl (50 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 (100 ml), dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (20 to 60% EtOAc/hexane) afforded the title compound as a tan solid. MS (ESI, pos. ion) m/z: 220 (M+1).

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