Ethyl 3-(trimethylsilyl)propynoate → Methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4-methoxybenzoate

HRID 1454955노트

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HRID 1454955 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:31][Si:32]([CH3:41])([CH3:40])[C:33]#[C:34][C:35](OCC)=[O:36]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[C:12]([O:14][CH3:15])=[O:13])[C:35](=[O:36])[C:34]#[C:33][Si:32]([CH3:41])([CH3:40])[CH3:31])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 568601Ethyl 3-(trimethylsilyl)propynoateHCID 2733832Lithium HexamethyldisilazideHCID 57531225Methyl 3-[(6-chloropyridazin-3-yl)methyl]-4-methoxybenzoate

생성물 1

HCID 57531244Methyl 3-[1-(6-chloropyridazin-3-yl)-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-4-methoxybenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of methyl 3-[(6-chloropyridazin-3-yl)methyl]-4-methoxybenzoate (10.03 g, 34.2 mmol) in THF (400 mL) was added LHMDS (100 mL, 1M solution in THF) and ethyl 3-(trimethylsilyl)propynoate (6.66 mL, 35.5 mmol) at −78° C. The reaction was warmed to 0° C. and stirred for 0.5 hr until the reaction was complete by LCMS analysis. The reaction was quenched with aqueous NH4Cl and extracted with ethyl acetate. The combined organic layers were washed with 0.5 N HCl, brine, dried over MgSO4, and condensed in vacuo to yield an oil. The crude material was purified via silica gel chromatography (CH2Cl2) to yield the title compound.

후처리

  1. customThe reaction was quenched with aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with 0.5 N HCl, brine
  4. dry with materialdried over MgSO4, and condensed in vacuo
  5. customto yield an oil
  6. customThe crude material was purified via silica gel chromatography (CH2Cl2)

출처 및 근거

ORD 기록
ord-0da6cc5dba5a4bcbbc4969e7a8ac72c1
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482345B2

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