반응 #91895

반응 방정식

7-bromochroman-4-one

TMSCN

LAH

→

4-(aminomethyl)-7-bromo-3,4-dihydro-2H-1-benzopyran-4-ol

수율 79.2%

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to rt
2. 2
   기타The reaction was quenched with the addition of EtOAc (10 mL) at 0° C.
3. 3
   workup.ADDITIONThe reaction mixture was diluted with EtOAc
4. 4
   건조dried (MgSO4)
5. 5
   여과filtered through Celite
6. 6
   농축concentrated

실험 절차

To a solution of 7-bromochroman-4-one (5.00 g, 22.0 mmol) and ZnI2 (30 mg) in toluene (50 mL) was added TMSCN (4.36 g, 44.0 mmol), and the mixture was heated at 60° C. overnight. The reaction mixture was cooled to rt, and a solution of LAH (20.0 mL, 2.4 M in THF, 44.0 mmol) was added slowly. The mixture was stirred at 40° C. for 2 h. The reaction was quenched with the addition of EtOAc (10 mL) at 0° C., followed by water (5 mL) and aqueous 10% NaOH (5 mL). The reaction mixture was diluted with EtOAc, dried (MgSO4), filtered through Celite, and concentrated to give 4.5 g (79%) of the crude 4-(aminomethyl)-7-bromo-3,4-dihydro-2H-1-benzopyran-4-ol intermediate as a yellow oil.

출처