반응 #951034

반응 방정식

N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine

potassium hydride

4-Phenyl-1-butyl iodide

→

N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture stirred for 15 hours
2. 2
   기타The reaction is quenched with MeOH
3. 3
   workup.ADDITIONdiluted with CH2Cl2
4. 4
   세척washed with water 2×
5. 5
   건조The organic phase is dried (Na2SO4)
6. 6
   농축concentrated
7. 7
   기타purified by column chromatography with 80% CH2Cl2 /20% petroleum ether

실험 절차

N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine (0.4 g; 0.74 mmol) is added to a suspension of potassium hydride (0.12 g; 1.1 mmol; 35% suspension in oil) in dry THF (4 ml) at 0° C. The reaction is stirred for 15 minutes at 20° C. 4-Phenyl-1-butyl iodide (0.21 g; 0.81 mmol) is added and the reaction mixture stirred for 15 hours. The reaction is quenched with MeOH, diluted with CH2Cl2 and washed with water 2×. The organic phase is dried (Na2SO4), concentrated and purified by column chromatography with 80% CH2Cl2 /20% petroleum ether to yield N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine as an oil which is used directly in Step F.

출처