Реакция #2487396

Уравнение реакции

4-fluorobenzoyl chloride

sodium hydride

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

→

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

Выход 14.9%

Растворители

THF

Условия реакции

Обработка

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

Методика

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).

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