Reaktion #623649

Reaktionsgleichung

5-fluoro-2-hydroxybenzaldehyde

acrylonitrile

DABCO

→

title compound

6-fluoro-2H-chromene-3-carbonitrile

Lösungsmittel

NaOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled
2. 2
   ExtraktionThe mixture was extracted with EtOAc (20 mL)
3. 3
   Trocknenthe organic layer was dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe resulting residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes)

Vorschrift

A solution of 5-fluoro-2-hydroxybenzaldehyde (1.00 g, 8.92 mmol) and acrylonitrile (9.40 mL, 143 mmol) was refluxed overnight with DABCO (1.00 g, 8.92 mmol). The mixture was cooled and 1 M NaOH (10 mL) was added. The mixture was extracted with EtOAc (20 mL), and the organic layer was dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes) to provide the title compound (4.50 g) as yellow crystals. 1H NMR (300 MHz, CDCl3) δ 7.13 (m, 1H), 6.98 (td, J=8.5, 3.0 Hz, 1H), 6.89-6.80 (m, 2H), 4.80 (d, J=1.4 Hz, 2H).

Quelle