반응 #1821850

반응 방정식

propargyl bromide

DMPU

NaH

propargyl bromide

NaH

N-trityl-N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-hydroxyethanamine

→

N-trityl-N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(prop-2-ynyloxy)ethanamine

용매

toluene

THF

반응 조건

후처리

1. 1
   workup.WAITthen brought to room temperature for 45 minutes
2. 2
   workup.STIRRINGstirred for 48 hours
3. 3
   workup.STIRRINGAfter stirring vigorously, an additional 48 hours the reaction mixture
4. 4
   기타is quenched with MeOH
5. 5
   농축concentrated
6. 6
   기타purified by column chromatography
7. 7
   기타The product is triturated with ether

실험 절차

Dry N-trityl-N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-hydroxyethanamine (8.7 g; 15.7 mmol) is dissolved in THF (50 ml). NaH (1 g; 25 mmol) is added and stirred vigorously at 0° C. for 1 minute then brought to room temperature for 45 minutes. DMPU [1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone] (5 ml) is added followed by propargyl bromide (80 wt %/toluene; 2.1 ml) and stirred for 48 hours. To this is added 0.6 g NaH and 1.5 ml propargyl bromide. After stirring vigorously, an additional 48 hours the reaction mixture is quenched with MeOH, concentrated and purified by column chromatography using 10 Et3N/10 CH2Cl2 /80 petroleum ether. The product is triturated with ether to give solid N-trityl-N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(prop-2-ynyloxy)ethanamine which is used directly in Step F.

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