반응 #2011035

반응 방정식

NaH

methyl 1-hydroxycyclopropanecarboxylate

iodomethane

→

methyl 1-methoxycyclopropanecarboxylate

용매

THF

반응 조건

후처리

1. 1
   온도cooled on an ice bath
2. 2
   workup.STIRRINGthe resulting mixture stirred at ambient temperature for 18 hours
3. 3
   기타The reaction mixture was quenched with ammonium chloride
4. 4
   추출extracted with EtOAc (3×20 mL)
5. 5
   세척The combined organic extracts were washed with water
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   기타The filtrate was evaporated under reduced pressure

실험 절차

NaH (738 mg, 18.44 mmol; 60% dispersion in oil) was added to a solution of methyl 1-hydroxycyclopropanecarboxylate (1.83 g, 14.18 mmol) in anhydrous THF (15 mL) cooled on an ice bath. The mixture was stirred for 15 minutes then iodomethane (3.22 g, 1.42 mL, 22.69 mmol) was added slowly, and the resulting mixture stirred at ambient temperature for 18 hours. The reaction mixture was quenched with ammonium chloride and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with water, dried over MgSO4, and filtered. The filtrate was evaporated under reduced pressure to give methyl 1-methoxycyclopropanecarboxylate. An aqueous 6N NaOH solution (4 mL) was added to a solution of methyl 1-methoxycyclopropanecarboxylate (1.08 g, 8.3 mmol) in anhydrous THF (5 mL). The mixture was stirred at room temperature for 18 hours, then acidified with aqueous 6N HCl and extracted with EtOAc (3×15 mL). The combined organic layer was dried over MgSO4, filtered and concentrated to give 1-methoxycyclopropanecarboxylic acid (892 mg, 54% yield) as an oil. 1H NMR (400 MHz, (CD3)2SO) δ 12.40 (br s, 1H), 3.30 (s, 3H), 1.15-1.10 (m, 2H), 1.08-1.04 (m, 2H).

출처