HCID 178491344、化合物 → HCID 178436445、化合物

HRID 254467

反応式

HRID 254467 の反応式
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]

参加物

5

反応物 2

HCID 178491344HCID 178491344、化合物HCID 178506846HCID 178506846、化合物

生成物 1

HCID 178436445HCID 178436445、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 18624872Benzene--cyclohexane (1/1)溶媒

反応条件

温度
-20 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-5f4e6ca46c3041f4a8d66df479d79769
出典データセット
uspto-grants-2011_01
特許番号
US07875645B2

関連ノート

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