Cesium carbonate → 1-(1,3-Dioxolan-2-ylmethyl)-7-methylquinolin-2(1h)-one

HRID 39686

반응식

HRID 39686 반응식
Br[CH2:2][CH:3]1[O:7][CH2:6][CH2:5][O:4]1.[CH3:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.CS(C)=O>[O:4]1[CH2:5][CH2:6][O:7][CH:3]1[CH2:2][N:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([CH3:8])[CH:18]=2)[CH:13]=[CH:14][C:15]1=[O:19]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 776737-Methyl-2-quinoloneHCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 516892Sodium Bicarbonate

생성물 1

HCID 593978351-(1,3-Dioxolan-2-ylmethyl)-7-methylquinolin-2(1h)-one

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
65 °C

실험 절차

To 6.3 mL of a dimethyl sulfoxide solution containing 1.1 g of 2-bromomethyl-1,3-dioxolane, 1.0 g of 7-methylquinolin-2(1H)-one and 3.1 g of cesium carbonate were added, and the mixture was stirred at 60 to 70° C. for 1 hour. The reaction mixture was added with ethyl acetate, water and an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:3] to obtain 0.60 g of a brown oily substance, 1-(1,3-dioxolan-2-ylmethyl)-7-methylquinolin-2(1H)-one.

후처리

  1. additionwere added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:3]

출처 및 근거

ORD 기록
ord-9041a22baa42428fbde1e34aa3e447f7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524738B2

연결된 노트

불러오는 중…