반응 #660098

반응 방정식

ammonium chloride

dimethyl carbonate

6-methylpicolinonitrile

LiHMDS

→

desired product

methyl 2-(6-cyanopyridin-2-yl)acetate

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for 30 mins at −78° C.
2. 2
   workup.WAITallowed to 0° C. for 30 mins
3. 3
   추출the mixture was extracted by ethyl acetate (100 ml*3)
4. 4
   건조the organic layer was dried by sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated under vacuo
7. 7
   기타to give the residue
8. 8
   기타The residue was purified by a standard method

실험 절차

To a solution of 6-methylpicolinonitrile (2 g, 16.9 mmol) in THF (20 ml) was added slowly LiHMDS (17 ml, 1M in THF) at −78° C. under N2. Then the reaction mixture was stirred for 1 h at −78° C. and then dimethyl carbonate (1.52 g, 16.9 mmol) was added at −78° C. The mixture was stirred for 30 mins at −78° C. and allowed to 0° C. for 30 mins. Saturated ammonium chloride was added to neutralize to adjust to PH=7-8, the mixture was extracted by ethyl acetate (100 ml*3), the organic layer was dried by sodium sulfate, filtered, concentrated under vacuo to give the residue. The residue was purified by a standard method to give the desired product.

출처