Reaktion #51204

Reaktionsgleichung

Sodium hydride

diethyl cyanomethyl phosphonate

3-Coumaranone

→

title product

Ausbeute 91.0%

1-Benzofuran-3-ylacetonitrile

Ausbeute 91.0%

Lösungsmittel

THF

EtOAc

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe whole stirred at room temperature for 45 min
2. 2
   Sonstigethe organic layer was then separated
3. 3
   Trocknendried (MgSO4)
4. 4
   Sonstigeevaporated
5. 5
   Sonstigethe residue flash chromatographed

Vorschrift

Sodium hydride (268 mg, 6.7 mmol) was slurried in dry THF (10 ml) at 0° C. under nitrogen and diethyl cyanomethyl phosphonate (1.1 ml, 6.7 mmol) added dropwise and the whole stirred for 45 min. 3-Coumaranone (Lancaster) (900 mg, 6.7 mmol) was then added dropwise and the whole stirred at room temperature for 45 min. The reaction was diluted with EtOAc (15 ml) and water (15 ml), and the organic layer was then separated, dried (MgSO4) and evaporated and the residue flash chromatographed using 0-5% EtOAc in pentane to give the title product (940 mg, 91%); 1HNMR (400 MHz, CDCl3) δ: 3.77 (s, 2H), 7.25-7.40 (m, 2H), 7.52 (dd, 1H), 7.58 (dd, 1H), 7.67 (s, 1H); LRMS: M+NH4+, 175. (TS+).

Quelle