Water → (Z)-ethyl 3-(2-methylquinolin-8-yl)but-2-enoate

HRID 339037

反応式

HRID 339037 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:13]([O:18][CH2:19][CH3:20])(=[O:17])/[CH:14]=[CH:15]/[CH3:16].C1(N(C)C2CCCCC2)CCCCC1.O>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.C(OCC)(=O)C>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2](/[C:15](/[CH3:16])=[CH:14]\[C:13]([O:18][CH2:19][CH3:20])=[O:17])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

参加物

8

反応物 4

HCID 962WaterHCID 24210N-Methyl dicyclohexylamineHCID 429065Ethyl trans-crotonateHCID 47150308-Bromo-2-methylquinoline

生成物 1

HCID 70983529(Z)-ethyl 3-(2-methylquinolin-8-yl)but-2-enoate収率 35.2%

試薬・触媒・溶媒 3

HCID 178418851HCID 178418851、化合物触媒HCID 8857Ethyl Acetate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), (E)-ethyl but-2-enoate (3.36 mL, 27.0 mmol), N-cyclohexyl-N-methylcyclohexanamine (5.79 mL, 27.0 mmol), and Pd(PtBu3)2 (0.23 g, 0.45 mmol) in dioxane (10 mL) was stirred at reflux for 20 hours. After cooling to ambient temperature, water (20 mL) and ethyl acetate (30 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 C-18 reverse phase flash chromatography (Biotage SP4 unit, C-18 40M column, 0-100% CH3CN/water gradient; 30 column volumes) to give (Z)-ethyl 3-(2-methylquinolin-8-yl)but-2-enoate (0.81 g, 35.2%) as a solid.

後処理

  1. temperatureat reflux for 20 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by C-18 reverse phase flash chromatography (Biotage SP4 unit

出典と根拠

ORDレコード
ord-95ffce153e0a46418ceb309f184b570f
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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