Sodium hydride → HCID 21949844, 화합물

HRID 2114664노트

반응식

HRID 2114664 반응식
[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]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 69484Ethyl 4-chloroacetoacetateHCID 9878953HCID 9878953, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 21949844HCID 21949844, 화합물수율 94.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3f0a3c1105ca40b984fd39322fc87173
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07435728B2

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