3,5-Dimethylisoxazole → 2-(3-Methyl-isoxazol-5-yl)-1-(2-tert.butyldimethylsiloxy-phenyl)-ethanone

HRID 54421

반응식

HRID 54421 반응식
C([Li])CCC.[CH3:6][C:7]1[CH:11]=[C:10]([CH3:12])[O:9][N:8]=1.[C:13]([C:17]1[C:26]([O:27][SiH:28]([CH3:30])[CH3:29])=[CH:25][CH:24]=[CH:23][C:18]=1[C:19](OC)=[O:20])([CH3:16])([CH3:15])[CH3:14].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:6][C:7]1[CH:11]=[C:10]([CH2:12][C:19]([C:18]2[CH:23]=[CH:24][CH:25]=[C:26]([O:27][SiH:28]([CH3:30])[CH3:29])[C:17]=2[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:20])[O:9][N:8]=1

참가 물질

7

반응물 4

HCID 93123,5-DimethylisoxazoleHCID 25517Ammonium ChlorideHCID 131719984Methyl 2-tert.butyldimethylsiloxybenzoateHCID 178418339Butyllithium

생성물 1

HCID 1317199832-(3-Methyl-isoxazol-5-yl)-1-(2-tert.butyldimethylsiloxy-phenyl)-ethanone수율 50.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-20 °C

실험 절차

52 ml of 1N solution of n-butyllithium in hexane were added to a solution of 6 g of 3,5-dimethylisoxazol in 200 ml of tetrahydrofuran at -78° C. After stirring for 1 h 15 g of methyl 2-tert.butyldimethylsiloxybenzoate in 50 ml of tetrahydrofuran were added at the same temperature. The reaction mixture was slowly warmed up to -20° C. A saturated aqueous solution of ammonium chloride was added, the mixture was extracted several times with ethylacetate. The organic phase was separated, washed with water and dried over magnesium sulfate. Chromatography on silica gel with heptane/ethylacetate gave 9.4 g of the product.

후처리

  1. additionwere added at the same temperature
  2. extractionthe mixture was extracted several times with ethylacetate
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate

출처 및 근거

ORD 기록
ord-a7602e0c89e6449eacff8936f61394cd
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622953

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