반응 #7257

반응 방정식

NH4Cl

2-fluoropyridine

lithium diisopropylamide

DMF

→

title compound

수율 15.0%

2-fluoro-pyridine-3-carbaldehyde

수율 15.0%

용매

EtOAc

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued at −78° C. for 2.5 h
3. 3
   온도to warm to room temperature
4. 4
   세척the organic phase was washed with saturated NaHCO3(aq) (20 mL) and brine (10 mL)
5. 5
   건조dried (MgSO4)
6. 6
   농축concentrated in vacuo
7. 7
   기타Purification of the crude material by chromatography on silica gel (10% EtOAc/hexanes)

실험 절차

A solution of 2-fluoropyridine (306 mg, 3.15 mmol) in THF (1 mL) was added to a solution of lithium diisopropylamide in THF (0.20 M, 17 mL, 3.4 mmol) at −78° C. The solution was stirred at −78° C. for 4 h, then DMF (0.73 mL, 9.4 mmol) was added dropwise and stirring was continued at −78° C. for 2.5 h. Saturated NH4Cl(aq) (2 mL) was added, and the mixture was allowed to warm to room temperature. The mixture was diluted with EtOAc (20 mL), and the organic phase was washed with saturated NaHCO3(aq) (20 mL) and brine (10 mL), then dried (MgSO4) and concentrated in vacuo. Purification of the crude material by chromatography on silica gel (10% EtOAc/hexanes) gave the title compound as a yellow liquid (58 mg, 15%). 1H NMR (CDCl3) □ 7.39 (m, 1H), 8.32 (m, 1H), 8.48 (m, 1H), 10.33 (s, 1H).

출처