Réaction #2487396

Équation de réaction

4-fluorobenzoyl chloride

sodium hydride

3-(hydroxymethyl)pyridine-2(1H)-one

→

(1,2-dihydro-2-oxopyridin-3-yl)methyl 4-fluorobenzoate

Rendement 14.9%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGto stir
3. 3
   Températurewith gentle heating and for 48 hours
4. 4
   AutreThe reaction was quenched with the addition of 20 mL of water
5. 5
   LavageThe reaction was washed with ethyl acetate (4×20 mL)
6. 6
   LavageThe organic layer was washed with brine (3×20 mL)
7. 7
   Séchagedried over MgSO4
8. 8
   AutreThe solvent was evaporated in vacuo
9. 9
   Autreto produce a white solid
10. 10
    AutreThe product was purified by crystallization from toluene

Mode opératoire

In Example 2, 0.0725 g of 60% sodium hydride (NaH) was dispersed in mineral oil (1.60 mmol) and was suspended in 40 mL of THF in a 100 mL RBF under the presence of argon gas. Then, 0.2003 g (1.60 mmol) of 3-(hydroxymethyl)pyridine-2(1H)-one was added slowly and the solution stirred for 30 min with gentle heating before 0.250 mL (2.08 mmol) of 4-fluorobenzoyl chloride was added dropwise. The reaction was allowed to stir with gentle heating and for 48 hours. The reaction was quenched with the addition of 20 mL of water. The reaction was washed with ethyl acetate (4×20 mL) and the organic layers combined. The organic layer was washed with brine (3×20 mL) and dried over MgSO4. The solvent was evaporated in vacuo to produce a white solid. The product was purified by crystallization from toluene. The yield of the reaction was 0.0590 g (14.94% yield). MP: 170-173° C. IR (cm−1): 3415.21 (m, broad), υ (O—H), 3125.47 (m, broad), υ (N—H), 1716.90 (m), υ (C═O), 1614.44 (m), (C═C aromatic). 1H NMR (DMSO-d6, 500 MHz) δ: 5.13 (s, 2H), 6.23 (t, J=6.6 Hz, 1H), 7.37 (t, J=8.9 Hz, 2H), 7.41 (dd, J=4.5, 2.1 Hz, 1H), 7.59 (dd, J=4.7, 2.1 Hz, 1H), 8.06 (t, J=7.7 Hz, 2H), 11.78 (s, 1H).

Source