反応 #2487396

反応方程式

4-fluorobenzoyl chloride

sodium hydride

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

→

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

収率 14.9%

溶媒

THF

反応条件

後処理

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

実験手順

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).

出典