反応 #2487399

反応方程式

NaH

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

4-fluorobenzoyl chloride

→

(1,6-dihydro-6-oxopyridin-2-yl)methyl 4-fluorobenzoate

収率 32.5%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe reaction stirred for 48 hours under the presence of argon gas
3. 3
   その他before being quenched with 20 mL of water
4. 4
   洗浄The reaction was washed with ethyl acetate (4×20 mL)
5. 5
   洗浄washed with saturated NaHCO3 (4×20 mL)
6. 6
   洗浄washed with Brine (3×20 mL)
7. 7
   乾燥finally dried over MgSO4
8. 8
   その他The solvent was removed in vacuo
9. 9
   その他to produce a dull yellow solid
10. 10
    その他The compound was purified by column chromatography(methanol/dichloromethane)

実験手順

In Example 5, 0.2006 grams (1.60 mmole) of 6-(hydroxymethyl)pyridine-2(1H)-one was suspended in 160 mL of THF in a 250 mL round bottom flask under the presence of argon gas. Then, 0.0671 g (1.68 mmole) of 60% NaH dispersed in mineral oil was added and the solution was stirred for 20 min. 0.19 mL (1.58 mmole) of 4-fluorobenzoyl chloride was dissolved in 20 mL of THF and added dropwise into the alcohol reaction mixture at a rate of 10 μL/min. The reaction stirred for 48 hours under the presence of argon gas before being quenched with 20 mL of water. The reaction was washed with ethyl acetate (4×20 mL), the organic layers combined, washed with saturated NaHCO3 (4×20 mL), washed with Brine (3×20 mL) and finally dried over MgSO4. The solvent was removed in vacuo to produce a dull yellow solid. The compound was purified by column chromatography(methanol/dichloromethane). The result was a fine white powder. (0.1287 grams, 32.48% Yield). 1H NMR (DMSO-d6, 500 MHz) δ: 5.12 (s, 2H) 6.29-6.41 (m, 2H) 7.38 (t, 2H) 7.45 (t, 1H) 8.08 (t, 2H) 11.74 (s, 1H).

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