تفاعل #51204

معادلة التفاعل

Sodium hydride

diethyl cyanomethyl phosphonate

3-Coumaranone

→

title product

المردود 91.0%

1-Benzofuran-3-ylacetonitrile

المردود 91.0%

المذيبات

THF

EtOAc

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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+).

المصدر