Ethyl trimethylsilylacetate → Ethyl 3-(4-(benzyloxy)phenyl)-3-(3-methyl-3H-1,2,3-triazol-4-yl)acrylate

HRID 2246651노트

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HRID 2246651 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(C)C.[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([C:37]2[N:38]([CH3:42])[N:39]=[N:40][CH:41]=2)=O)=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([C:37]2[N:38]([CH3:42])[N:39]=[N:40][CH:41]=2)=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:31][CH:30]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

5

반응물 3

HCID 77687Ethyl trimethylsilylacetateHCID 2733832Lithium HexamethyldisilazideHCID 57835886(4-(Benzyloxy)phenyl)(3-methyl-3H-1,2,3-triazol-4-yl)methanone

생성물 1

HCID 68687528Ethyl 3-(4-(benzyloxy)phenyl)-3-(3-methyl-3H-1,2,3-triazol-4-yl)acrylate수율 95.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of lithium bis(trimethylsilyl)amide (22 mmol, 1 m in THF) was added ethyl trimethylsilylacetate (31.5 mmol) dropwise at −78° C. After 20 minutes at −78° C., a solution of 3.3 (14.7 mmol) in THF (50 mL) was added dropwise, and the reaction was maintained at −78° C. for 4 hours. The reaction was quenched with saturated NH4Cl (aq) and warmed to room temperature. The mixture was extracted with EtOAc (500 mL), dried over anhydrous sodium sulfate, filtered, and concentrated with silica gel under reduced pressure. The residue was chromatographed (silica gel, 1:1 EtOAc/hexane) to afford compound 3.4 (5.1 g, 14 mmol). MS ESI (pos.) m/e 364.1 (M+H).

후처리

  1. customThe reaction was quenched with saturated NH4Cl (aq)
  2. temperaturewarmed to room temperature
  3. extractionThe mixture was extracted with EtOAc (500 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated with silica gel under reduced pressure
  7. customThe residue was chromatographed (silica gel, 1:1 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-3e831d8f3add4d1892ca29abc66b938c
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687526B2

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