HCID 178491344, 화합물 → HCID 178436445, 화합물

HRID 254467

반응식

HRID 254467 반응식
CO[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1/[CH:11]=[N:12]/[CH:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15].[CH2:20]([Li])[CH3:21]>C1COCC1.C1CCCCC1.C1C=CC=CC=1>[CH2:20]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1/[CH:11]=[N:12]/[CH:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH3:21]

참가 물질

5

반응물 2

HCID 178491344HCID 178491344, 화합물HCID 178506846HCID 178506846, 화합물

생성물 1

HCID 178436445HCID 178436445, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 18624872Benzene--cyclohexane (1/1)용매

반응 조건

온도
-20 °C

실험 절차

To a solution of 10.0 g (38 mmol) [1-(2,6-dimethoxy-phenyl)-meth-(E)-ylidene]-(1-isopropyl-2-methyl-propyl)-amine in 30 ml dry THF cooled to −20° C. were added 91.2 ml of a 0.5M solution of ethyl lithium in cyclohexane/benzene drop-wise to keep temperature below 0° C. Then the mixture was stirred at −20° C. for further 30 min and the reaction quenched by addition of water. The aqueous phase was extracted with ethyl acetate, the combined extracts washed with brine, dried over Na2SO4, filtered and evaporated. Purification of the crude product by flash chromatography on silica gel with a heptane/ethyl acetate gradient provided 4.30 g (E)-[1-(2-ethyl-6-methoxy-phenyl)-methylidene]-(1-isopropyl-2-methyl-propyl)-amine as colourless liquid: MS (EI): 261.4 (M+.), 218.3 ((M-((CH3)2CH)+.), 100%).

후처리

  1. customtemperature below 0° C
  2. customthe reaction quenched by addition of water
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined extracts washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the crude product by flash chromatography on silica gel with a heptane/ethyl acetate gradient

출처 및 근거

ORD 기록
ord-5f4e6ca46c3041f4a8d66df479d79769
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875645B2

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