Toluene → Ethyl 2-[6-tert-butylpyridin-3-yl]-2-ethylcyclopropanecarboxylate

HRID 607525ノート

反応式

HRID 607525 の反応式
[C:1]1([CH3:7])[CH:6]=[CH:5]C=[CH:3][CH:2]=1.CN1[CH:13]=[CH:12][N:11]=[CH:10]1.[N+](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N-]>CCOC(C)=O>[C:1]([C:12]1[N:11]=[CH:10][C:6]([C:1]2([CH2:2][CH3:3])[CH2:7][CH:16]2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][CH:13]=1)([CH3:7])([CH3:6])[CH3:2]

参加物

5

反応物 3

HCID 1140TolueneHCID 13901-MethylimidazoleHCID 12192Ethyl diazoacetate

生成物 1

HCID 67046826Ethyl 2-[6-tert-butylpyridin-3-yl]-2-ethylcyclopropanecarboxylate収率 49%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a toluene (100 ml) solution of the compound of example 62B (1.89 g, 10 mmol), Co(TPP) (0.17 g, 0.25 mmol), 1-methyl-1H-imidazole (2.39 ml, 30 mmol), and ethyl diazoacetate (1.58 ml, 15 mmol) were added and the mixture was stirred for 5 minutes at room temperature followed by additional stirring for 1.5 hours at 80° C. The reaction mixture was diluted with EtOAc and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate and concentrated in vacuo to give the crude product. The crude product was purified by column chromatography on silica gel, eluting with hexane/EtOAc (1:10), to give the title compound (1.34 g, 49%, trans) as a brown oil.

後処理

  1. stirringby additional stirring for 1.5 hours at 80° C
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluting with hexane/EtOAc (1:10)

出典と根拠

ORDレコード
ord-9020c1240d7b44fdab8a492c54cd9601
出典データセット
uspto-grants-2011_03
特許番号
US07915448B2

反応ノート

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