Diethyl Malonate → HCID 70983315、化合物

HRID 338901

反応式

HRID 338901 の反応式
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.C([O-])([O-])=O.[Cs+].[Cs+].[C:19]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(OCC)(=O)C>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]([O:27][CH2:28][CH3:29])=[O:26])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

参加物

8

反応物 4

HCID 7761Diethyl MalonateHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 47150308-Bromo-2-methylquinoline

生成物 1

HCID 70983315HCID 70983315、化合物収率 82.54%

試薬・触媒・溶媒 3

HCID 178418851HCID 178418851、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 8-bromo-2-methylquinoline (2.00 g, 9.01 mmol), Pd(PtBu3)2 (0.23 g, 0.45 mmol), Cs2CO3 (11.74 g, 36.02 mmol) and diethyl malonate (2.73 mL, 18.01 mmol) in dioxane (25 mL) was heated at 118° C. in a sealed tube for 1 hour. After cooling to ambient temperature, ethyl acetate (30 mL) and water (15 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (7:1 hexane/ethyl acetate) to give diethyl 2-(2-methylquinolin-8-yl)malonate (2.24 g, 82.54%) as an oil.

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (7:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-860037163f144b3dbd39da5485ccfc21
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

関連ノート

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