tert-Butyldimethylsilyl chloride → Tert-butyl{[1-(4-fluorobenzylidene)prop-2-en-1-yl]oxy}dimethylsilane

HRID 1991355ノート

反応式

HRID 1991355 の反応式
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:18])[CH:16]=[CH2:17])=[CH:10][CH:9]=1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([Si:23]([O:18][C:15](=[CH:14][C:11]1[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=1)[CH:16]=[CH2:17])([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 210992911-(4-Fluorophenyl)but-3-en-2-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 73742632Tert-butyl{[1-(4-fluorobenzylidene)prop-2-en-1-yl]oxy}dimethylsilane収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a solution of 104 mL (104.0 mmol, 1.2 equiv.) of a 1.0M solution of potassium tert-butoxide in THF and 100 mL dry THF under nitrogen atmosphere at −78° C. was added a solution of 14.2 g (86.6 mmol, 1 equiv.) of 1-(4-fluorophenyl)but-3-en-2-one (step B) and 13.0 g (86.6 mmol) tert-butylchlorodimethylsilane in 100 mL dry THF. The reaction mixture was stirred at −78° C. for 6 hr and at RT for 6 hr then quenched by the addition of 50 mL water. The resulting mixture was warmed to RT, diluted with 150 mL hexanes, transferred to a separatory funnel and the organic layer separated. The organic layer was washed with 50 mL brine, dried over anhydrous magnesium sulfate, filtered and the solvent evaporated under vacuum to give 20.5 g of the crude title compounds which were used without further purification. 1H-NMR (CDCl3): δ: 7.52 (2H, m), 6.98 (2H, m), 6.33 (1H, dd, J3=13.2 Hz, J2=8.5 Hz), 5.97 (1H, s), 5.52 (1H, d, J=13.2 Hz), 5.17 (1H, d, J=8.5 Hz).

後処理

  1. customthen quenched by the addition of 50 mL water
  2. temperatureThe resulting mixture was warmed to RT
  3. additiondiluted with 150 mL hexanes
  4. customtransferred to a separatory funnel
  5. customthe organic layer separated
  6. washThe organic layer was washed with 50 mL brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated under vacuum

出典と根拠

ORDレコード
ord-59940d79c8934458bab7a4e68b6ef9a4
出典データセット
uspto-grants-2010_01
特許番号
US07645790B2

反応ノート

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