반응 #167390

반응 방정식

MeOH

cyclopropyl magnesium bromide

2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde

→

product

수율 99.4%

1-[4-(Cyclopropyl-hydroxy-methyl)-3-fluoro-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

수율 99.4%

용매

CHCl3

THF

THF

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched with aqueous NH4Cl solution
2. 2
   농축the THF layer was concentrated
3. 3
   추출The aqueous layer was extracted with ethylacetate
4. 4
   건조The organic layer was dried over Na2SO4
5. 5
   농축concentrated
6. 6
   기타to afford the crude product
7. 7
   기타Purification by column chromatography on silica gel (3% MeOH in CHCl3)
8. 8
   세척wash

실험 절차

A 0.5M solution of cyclopropyl magnesium bromide in THF (2.4 mL, 1.170 mmol) was added dropwise to 2-fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde (I-121a: 175 mg, 0.585 mmol) in dry THF (10 mL) at 0° C. under nitrogen atmosphere. The resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC (5% MeOH in CHCl3). The reaction mixture was quenched with aqueous NH4Cl solution and the THF layer was concentrated. The aqueous layer was extracted with ethylacetate. The organic layer was dried over Na2SO4 and concentrated to afford the crude product. Purification by column chromatography on silica gel (3% MeOH in CHCl3), followed by hexane wash, afforded 200 mg of the product (99.41% yield).

출처