1-(3-Methylpyridin-2-yl)ethan-1-one → 2-(3-Methylpyridin-2-yl)but-3-yn-2-ol

HRID 575058노트

반응식

HRID 575058 반응식
[CH3:1][C:2]1[C:3]([C:8](=[O:10])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:11]([Mg]Br)#[CH:12]>C1COCC1>[CH3:1][C:2]1[C:3]([C:8]([OH:10])([C:11]#[CH:12])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 130686691-(3-Methylpyridin-2-yl)ethan-1-oneHCID 178418486HCID 178418486, 화합물

생성물 1

HCID 866930912-(3-Methylpyridin-2-yl)but-3-yn-2-ol수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

This compound was prepared according to a procedure similar to that described in Procedure A. 1-(3-Methylpyridin-2-yl)ethan-1-one. (3.2 g, 23.68 mmol, 1.00 equiv) was dissolved in 6 mL of THF under inert nitrogen atmosphere in a 100-mL 3-necked round-bottom flask. Then ethynylmagnesium bromide (2M in THF, 61 mL, 1.30 equiv) was added dropwise into the solution at 0° C. The resulting solution was stirred for 10 min and then allowed to rise to room temperature and stirred for additional 2 h. The reaction was then quenched by the addition of 20 mL of sat. aqueous NH4Cl and the resulting solution was extracted with 2×25 mL of ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum to get a residue, which was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5) to obtain 3.5 g (88%) of 2-(3-methylpyridin-2-yl)but-3-yn-2-ol as a light yellow solid.

후처리

  1. customThis compound was prepared
  2. customto rise to room temperature
  3. stirringstirred for additional 2 h
  4. customThe reaction was then quenched by the addition of 20 mL of sat. aqueous NH4Cl
  5. extractionthe resulting solution was extracted with 2×25 mL of ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customto get a residue, which

출처 및 근거

ORD 기록
ord-247a905654654baeb33777ff23447334
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034866B2

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