Reaktion #2487395

Reaktionsgleichung

alcohol

3-hydroxymethyl-2-pyridone

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

butyl lithium

4-iodobenzoyl chloride

→

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to −80° C. in a methanol bath
2. 2
   workup.STIRRINGThe reaction was stirred for 48 hours at −80° C. under the presence of argon gas
3. 3
   Sonstigewas then returned to room temperature
4. 4
   Sonstigewas quenched with 20 mL of water
5. 5
   WaschenThe reaction was washed with ethyl acetate (4×20 mL)
6. 6
   Waschenwashed with Brine (3×20 mL)
7. 7
   Trocknenfinally dried over MgSO4
8. 8
   SonstigeThe solvent was removed in vacuo
9. 9
   Sonstigeto produce a dull brown solid
10. 10
    SonstigeThe compound was purified by crystallization from toluene

Vorschrift

A 25 mL round bottom flask was charged with 0.209 g (1.67 mmole) of 3-(hydroxymethyl)pyridine-2(1H)-one and suspended in 15 mL of THF under the presence of argon gas. The solution was cooled to −80° C. in a methanol bath and 1.05 mL (1.68 mmol) of butyl lithium (BuLi) was added dropwise, and the solution stirred for 20 min. 0.4454 g (1.67 mmol) of 4-iodobenzoyl chloride was dissolved in 15 mL of THF, cooled to −80° C. in a methanol bath, then added dropwise into the alcohol reaction mixture. The reaction was stirred for 48 hours at −80° C. under the presence of argon gas. The reaction was then returned to room temperature and was quenched with 20 mL of water. The reaction was washed with ethyl acetate (4×20 mL), the organic layers combined, washed with Brine (3×20 mL), and finally dried over MgSO4. The solvent was removed in vacuo to produce a dull brown solid. The compound was purified by crystallization from toluene. The yield of the product was 0.0652 g (10.99% Yield). MP: 203-205° C. IR: (cm−1): 3415.21 (m, broad), υ (O—H), 3128.97 (m, broad), υ (N—H), 1720.30 (m), υ (C═O), 1613.77 (m), υ (C═C aromatic). 1H NMR (DMSO-d6, 500 MHz) δ: 5.13 (s, 2H), 6.23 (t, J=6.6 Hz, 1H), 7.40 (dd, J=4.5, 2.1 Hz, 1H), 7.59 (dd, J=4.7, 2.1 Hz, 1H), 7.74 (d, J=4.8 Hz, 2H), 7.94 (d, J=4.8 Hz, 2H), 11.78 (s, 1H). 13C NMR (DMSO-d6) δ: 165.76, 161.84, 139.75, 138.29, 135.79, 131.41, 129.58, 126.43, 105.09, 102.35, 62.81. HRMS: m/e, found 377.9583 (M+Na+). Calc. for C13H10INO3Na: 377.9603.

Quelle