반응 #60347

반응 방정식

LAH

Rochelle's salt

chroman-4-one oxime

→

title compound

chroman-4-ylamine

용매

THF

H2O

THF

반응 조건

후처리

1. 1
   온도The mixture was heated slowly
2. 2
   온도to reflux for 4 h
3. 3
   기타The layers were separated
4. 4
   추출the aqueous layer was extracted with EtOAc until tlc analysis of the aqueous layer
5. 5
   건조The combined organics were dried over MgSO4
6. 6
   농축concentrated in vacuo
7. 7
   기타to furnish the crude material, which
8. 8
   기타was purified by flash column chromatography

실험 절차

LAH (6.35 g, 167 mmol) was suspended in THF (100 mL) at 0° C. A solution of chroman-4-one oxime (Step A) (10.92 g, 66.92 mmol) in THF (100 mL) was added drop-wise. The mixture was heated slowly to reflux for 4 h. The reaction was cooled to RT and added drop-wise to a stirred saturated solution of Rochelle's salt in H2O. The bi-phasic mixture was stirred rapidly at RT for 1 h. The layers were separated and the aqueous layer was extracted with EtOAc until tlc analysis of the aqueous layer showed no evidence of the title compound. The combined organics were dried over MgSO4 and concentrated in vacuo to furnish the crude material, which was purified by flash column chromatography to afford the title compound. MS (APCI pos) 150 (M+H).

출처