2-(Tert-butyldimethylsilanyloxy)-1-phenylethanone → tert-Butyl-dimethyl-(2-phenyl-allyloxy)-silane

HRID 77325

反応式

HRID 77325 の反応式
[CH2:1]([Li])CCC.[C:6]([Si:10]([CH3:22])([CH3:21])[O:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)([CH3:9])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:6]([Si:10]([CH3:22])([CH3:21])[O:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:1])([CH3:9])([CH3:8])[CH3:7]

参加物

5

反応物 2

HCID 135233382-(Tert-butyldimethylsilanyloxy)-1-phenylethanoneHCID 178418339Butyllithium

生成物 1

HCID 67155247tert-Butyl-dimethyl-(2-phenyl-allyloxy)-silane

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a well stirred solution of methyl-triphenyl-phosphonium bromide (3.08 g, 8.61 mmol) in tetrahydrofuran (10 mL) at 0° C. is added n-butyllithium (4.89 mL, 7.83 mmol of a 1.6 M solution). The reaction mixture is allowed to warm to room temperature, stirred for 1 h, then cooled to 0° C. 2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethanone (980 mg, 3.91 mmol) in tetrahydrofuran (30 mL) is then slowly added. The mixture is stirred at room temperature for 30 min then quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted several times with ethyl acetate. The organic layers are combined, washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (20% ethyl acetate in hexanes) to yield 1.3 g of the title compound as a clear oil containing ethyl acetate and was used directly in the next step.

後処理

  1. temperaturecooled to 0° C
  2. stirringThe mixture is stirred at room temperature for 30 min
  3. customthen quenched by the addition of a saturated aqueous solution of ammonium chloride
  4. extractionextracted several times with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified via silica gel chromatography (20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-b2a7d5ee0ce54511bfb46783c5186f6e
出典データセット
uspto-grants-2014_09
特許番号
US08841291B2

関連ノート

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