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

HRID 54421

反応式

HRID 54421 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a7602e0c89e6449eacff8936f61394cd
出典データセット
uspto-grants-1997_04
特許番号
US05622953

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