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

HRID 339037

반응식

HRID 339037 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418851HCID 178418851, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-95ffce153e0a46418ceb309f184b570f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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