Diazoacetophenone → Ethyl 4-(4-chloro-2-nitrobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate

HRID 428430노트

반응식

HRID 428430 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]#[C:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.[N+:20](=[CH:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24])=[N-:21]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:9]2[C:22]([C:23](=[O:24])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:20][NH:21][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:16])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

참가 물질

4

반응물 2

HCID 18667DiazoacetophenoneHCID 18358889Ethyl 4-(4-chloro-2-nitrophenyl)-4-oxo-2-butynoate

생성물 1

HCID 18358884Ethyl 4-(4-chloro-2-nitrobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate수율 74.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of ethyl 4-(4-chloro-2-nitrophenyl)-4-oxo-2-butynoate (prepared as described in Example 48(a)) (1.2 g, 4.11 mmol) and diazoacetophenone (1.2 g, 8.22 mmol, prepared as described in Org. Syn. Coll. Vol. VI, pp. 386-388) in tetrahydrofuran (THF) (21.6 mL) was stirred at room temperature for 16 hours. The reaction was concentrated by rotary evaporation and purified by flash chromatography eluting with hexanes:ethyl acetate (90:10, 80:20, 70:30) to give the title compound (1.3 g, 74.3%); Rf 0.38 (1:1 ethyl acetate:hexanes).

후처리

  1. concentrationThe reaction was concentrated by rotary evaporation
  2. custompurified by flash chromatography
  3. washeluting with hexanes:ethyl acetate (90:10, 80:20, 70:30)

출처 및 근거

ORD 기록
ord-62b06b32366a430d92125d3ee4b88809
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313290B1

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