Sodium hydride → HCID 21949844、化合物

HRID 558300ノート

反応式

HRID 558300 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:9]([CH2:15][CH3:16])=[N:10][NH:11][C:12]=1[CH2:13][CH3:14].[H][H].Cl[CH2:24][C:25](=[O:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:12]([CH2:13][CH3:14])=[N:11][N:10]([CH2:24][C:25](=[O:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:9]=1[CH2:15][CH3:16]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 9878953HCID 9878953、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 21949844HCID 21949844、化合物収率 94.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% dispersion in oil, 250 mg, 6.17 mmol) was added to a stirred solution of 4-(3,5-dichlorophenoxy)-3,5-diethyl-1H-pyrazole (800 mg, 2.81 mmol, Example 3) in dry N,N-dimethylformamide (5 ml) at 0° C. under nitrogen. The mixture was stirred for 5 minutes during which time hydrogen was evolved and then ethyl 4-chloroacetoacetate (0.42 ml, 3.09 mmol) was added. After 30 minutes the reaction mixture was quenched by the addition of water (0.5 ml) and concentrated under reduced pressure. A solution of the residue in ethyl acetate (50 ml) was washed with saturated aqueous ammonium chloride solution (20 ml) and water (20 ml), dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate:pentane (30:70, by volume) to provide the title compound (1.1 g) as a white solid, m.p. 82-84° C.

後処理

  1. customAfter 30 minutes the reaction mixture was quenched by the addition of water (0.5 ml)
  2. concentrationconcentrated under reduced pressure
  3. washA solution of the residue in ethyl acetate (50 ml) was washed with saturated aqueous ammonium chloride solution (20 ml) and water (20 ml)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate:pentane (30:70, by volume)

出典と根拠

ORDレコード
ord-4882abf963f64dc3ab391ed10f7cdc9d
出典データセット
uspto-grants-2011_11
特許番号
US08063044B2

反応ノート

読み込み中…