반응 #955937

반응 방정식

EtMgBr

methyl 4-chloro-2-methoxybenzoate

→

methyl 4-ethyl-2-methoxybenzoate

수율 50.0%

용매

THF

NMP

ether

반응 조건

후처리

1. 1
   기타giving a red color
2. 2
   기타quenched upon the addition of aq. HCl (1M, 50 mL)
3. 3
   추출The crude product was extracted with ether
4. 4
   세척the combined organic layers were successively washed with water and brine
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The residue was purified on silica gel (Eluent: 30% EtOAc in hexanes)

실험 절차

To a solution of methyl 4-chloro-2-methoxybenzoate (example 18d) (4.16 g, 20.8 mmol) in THF (120 mL) and NMP (12 mL) was added under inert atmosphere Iron (III) acetylacetonate (398 mg, 1.17 mmol) giving a red color. Then EtMgBr (29 ml of 1M solution in ether) was added dropwise under vigorous stirring. The mixture turned dark brown and then violet and then was stirred for 15 more min. The reaction was diluted with ether and quenched upon the addition of aq. HCl (1M, 50 mL). The crude product was extracted with ether and the combined organic layers were successively washed with water and brine, dried over MgSO4, filtered and evaporated. The residue was purified on silica gel (Eluent: 30% EtOAc in hexanes) to give methyl 4-ethyl-2-methoxybenzoate (2.01 g, 50%) as an oil. 1H NMR (300 MHz, dMSO): δ 1.20-1.22(t, 3H), 2.65-2.7 (dd, 2H), 3.9 (s, 3H), 6.8 (s, 1H), 6.97 (m, 1H), 7.7 (m, 1H).

출처