Water → HCID 178441857, 화합물

HRID 486019노트

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HRID 486019 반응식
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH2:16][OH:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C)C=O>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH:16]=[O:17])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 178441858HCID 178441858, 화합물

생성물 1

HCID 178441857HCID 178441857, 화합물수율 90.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 0.3 g of 2-butyl-6-(hydroxymethyl)-4(1H)-quinazolinone in 3.5 ml of dry N,N-dimethylformamide is added 1.7 g of pyridinium dichromate. The reaction mixture is stirred at room temperature for 16 hours and then poured into 125 ml of water. The resulting precipitate is removed by filtration and the filtrate extracted with 9:1 chloroform-methanol. The combined organic extracts are dried over magnesium sulfate, filtered and concentrated in vacuo and combined with the precipitate above. The combined solids are purified by flash chromatography on silica gel by eluting with 1:1 ethyl acetate-hexanes to give 0.27 g of the desired product. CI MASS SPEC 231(M+H).

후처리

  1. customThe resulting precipitate is removed by filtration
  2. extractionthe filtrate extracted with 9:1 chloroform-methanol
  3. dry with materialThe combined organic extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe combined solids are purified by flash chromatography on silica gel
  7. washby eluting with 1:1 ethyl acetate-hexanes

출처 및 근거

ORD 기록
ord-5384cabd8e984d589c8ae2e30345e80f
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290780

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