Ethyl Acetoacetate → Ethyl 2-(5,6-Diphenyl-1,2,4-triazin-3-yl)acetate

HRID 12564

반응식

HRID 12564 반응식
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5](C)=O.CS(C1[N:17]=[N:18][C:19]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:21]=1)(=O)=O>C1COCC1>[C:22]1([C:20]2[N:21]=[C:5]([CH2:4][C:3]([O:9][CH2:10][CH3:11])=[O:8])[N:17]=[N:18][C:19]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

5

반응물 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 129154813-(Methanesulfonyl)-5,6-diphenyl-1,2,4-triazine2회

생성물 1

HCID 12915487Ethyl 2-(5,6-Diphenyl-1,2,4-triazin-3-yl)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
60 °C

실험 절차

To a suspension of NaH (41 mg, 1.61 mmol) in THF (2 ml) at 0° C. was added ethyl acetoacetate (105 mg. 0.80 mmol) dropwise. After the mixture was stirred for 15 min, a solution of 3-(methylsulfonyl)-5,6-diphenyl-1,2,4-triazine (Compound 87) (250 mg, 0.80 mmol) in THF (3 ml) was cannulated into the solution, and the resulting solution was heated to 60° C. for 2 hours. The reaction was then quenched with water. The product was extracted with ethyl acetate. The organic layer was washed with water, and brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo, and the residue was purified by silica gel chromatography (20% ethyl acetate in hexane) to give title compound as a solid.

후처리

  1. customThe reaction was then quenched with water
  2. extractionThe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtered solvent was concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-b001ef4de7204123bc89d9ca3f7063f6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728014B2

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