반응 #68603

반응 방정식

MeMgBr

HCl

N-methoxy-N-methylquinoline-6-carboxamide

THF

Methylmagnesium bromide

→

1-(quinolin-6-yl)ethanone

수율 86.6%

반응 조건

후처리

1. 1
   온도cooled to 0 C
2. 2
   workup.STIRRINGthe mixture was stirred overnight
3. 3
   추출the aqueous layer was extracted with DCM (200 mL×2) and EtOAc (200 mL×2)
4. 4
   건조The organic layer was dried with MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타to give a yellow oil
8. 8
   농축so the layer was concentrated
9. 9
   여과filtered
10. 10
    세척first eluting with water than with MeOH
11. 11
    농축The MeOH layer was concentrated
12. 12
    기타to give a yellow oil which
13. 13
    기타The combined portions were purified by MPLC
14. 14
    세척eluting with a gradient of 2-6% MeOH/DCM

실험 절차

A 250 mL RB flask was charged with N-methoxy-N-methylquinoline-6-carboxamide (5.943 g, 27.5 mmol) and THF (100 ml, 1220 mmol), then cooled to 0 C. Methylmagnesium bromide (18.3 ml, 55.0 mmol) was added dropwise and the mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction was not quite complete, so additional MeMgBr (3 mL) was added and the mixture was stirred overnight. The mixture was then neutralized using 2N HCl and the aqueous layer was extracted with DCM (200 mL×2) and EtOAc (200 mL×2). The organic layer was dried with MgSO4, filtered, and concentrated to give a yellow oil. The aqueous layer contained some product, so the layer was concentrated and then filtered thru a reverse phase C18 column, first eluting with water than with MeOH. The MeOH layer was concentrated to give a yellow oil which was combined with the yellow oil from the organic layer. The combined portions were purified by MPLC eluting with a gradient of 2-6% MeOH/DCM. 1-(quinolin-6-yl)ethanone (4.074 g, 86.6% yield) was isolated as a yellow oil which solidified upon standing.

출처