تفاعل #2487396

معادلة التفاعل

4-fluorobenzoyl chloride

sodium hydride

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

→

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

المردود 14.9%

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر