반응 #90445

반응 방정식

product

1-chloro-3-(phenylamino)propan-2-ol

KOH

→

colorless oil

수율 95.0%

N-(oxiran-2-ylmethyl)aniline

수율 95.0%

용매

EtOAc

1,4-dioxane

반응 조건

후처리

1. 1
   세척washed with 1M HCl and brine
2. 2
   건조The organic layer was dried with MgSO4
3. 3
   농축concentrated
4. 4
   기타to give crude product
5. 5
   기타It was further purified by silica gel chromatography

실험 절차

To a solution of the product of Step 3 (185.7 mg, 1.0 mmol, 1 equiv) in 1,4-dioxane (3.3 mL) was added KOH powder (67.3 mg, 1.2 mmol, 1.2 equiv). The mixture was stirred at room temperature for 24 hours. The mixture was diluted with EtOAc and washed with 1M HCl and brine. The organic layer was dried with MgSO4 and concentrated to give crude product. It was further purified by silica gel chromatography using 20% EtOAc/Hex to afford 141.8 mg colorless oil as product, yield 95.0%. 1H NMR (CDCl3, 400 MHz) δ=2.70 (dd, J=4.9, 2.3 Hz, 1H) 2.87-2.77 (m, 1H) 3.23-3.18 (m, 1H) 3.26 (t, J=4.9 Hz, 1H) 3.59-3.48 (m, 1H) 3.87 (s, 1H) 6.64 (d, J=7.7 Hz, 2H) 6.73 (t, J=7.3 Hz, 1H) 7.18 (dd, J=8.3, 7.5 Hz, 2H).

출처