Tetrahydrofuran → 4-[1-(3-Cyclopentyloxy-4-methoxy-phenyl)ethyl]-5-methylpyrazol-3-one

HRID 1067390

反応式

HRID 1067390 の反応式
C(OP([CH2:9][C:10](=[O:15])[N:11](OC)C)(=O)OCC)C.[CH:16]([N-:19]C(C)C)(C)[CH3:17].[Li+].[CH:24]1([O:29][C:30]2[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=2[O:38][CH3:39])[CH:33]=O)[CH2:28][CH2:27][CH2:26][CH2:25]1.O1CCC[CH2:41]1>O>[CH:24]1([O:29][C:30]2[CH:31]=[C:32]([CH:33]([C:9]3[C:10](=[O:15])[N:11]=[N:19][C:16]=3[CH3:17])[CH3:41])[CH:35]=[CH:36][C:37]=2[O:38][CH3:39])[CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 2724682Lithium diisopropylamideHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 2773719Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate

生成物 1

HCID 211937424-[1-(3-Cyclopentyloxy-4-methoxy-phenyl)ethyl]-5-methylpyrazol-3-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of diethyl(N-methoxy-N-methyl-carbamoylmethyl)phosphonate (2.60 g, 10.90 mmol) in dry tetrahydrofuran (50 ml) at −78° C. was added lithium diisopropylamide (1.5M solution in cyclohexane, 7.33 ml, 11 mmol) dropwise over 3 minutes. The resulting solution was stirred at −78° C. for 30 minutes, after which time 3-cyclopentyloxy-4-methoxybenzaldehyde (1.5 g, 6.81 mmol) in dry tetrahydrofuran (5 ml) was added in one portion. The reaction was allowed to warm to room temperature and stirring continued overnight. After which time the reaction mixture was diluted with water (25 ml) and the tetrahydrofuran removed in vacuo. The aqueous residue was diluted with brine (25 ml) and extracted with methylene chloride (3×60 ml). The organic extracts were dried (Na2SO4) and evaporated in vacuo to give a yellow liquid. The liquid was purified by flash chromatography (SiO2; hexane/ethyl acetate (65:35)) to afford the title compound as a pale yellow liquid (1.986 g).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirring continued overnight
  3. customthe tetrahydrofuran removed in vacuo
  4. additionThe aqueous residue was diluted with brine (25 ml)
  5. extractionextracted with methylene chloride (3×60 ml)
  6. dry with materialThe organic extracts were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give a yellow liquid
  9. customThe liquid was purified by flash chromatography (SiO2; hexane/ethyl acetate (65:35))

出典と根拠

ORDレコード
ord-6567b1f9e65a4a7f95522b4d10c28bec
出典データセット
uspto-grants-2001_06
特許番号
US06248769B1

関連ノート

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