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Benzaldehyde → 5-Methoxy-3-phenyl-3H-isobenzofuran-1-one

HRID 985147
ノート
印刷プレビュー

反応式

HRID 985147 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](NC)=[O:8])=[CH:5][CH:4]=1.C([Li])(CC)C.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCCCCC.C(OCC)(=[O:34])C>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:34])[O:8][CH:18]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 3460314-methoxy-N-methylbenzamide2 回HCID 21226206Ethyl acetate hexaneHCID 178418400CID 53628100

生成物 1

HCID 131723595-Methoxy-3-phenyl-3H-isobenzofuran-1-one収率 55.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

A solution of 8 (15 g, 91 mmol) in THF was cooled to −70° C. under Argon. To this was added sec-butyllithium (147 mL, 1.3M). After stirring 0.5 h a tan suspension resulted. Added benzaldehyde (9.2 mL, 91 mmol.) and stirred 1 h. Quenched with ice then removed THF in vacuo. Added sat. sodium bicarbonate and extracted with ethyl acetate (4×). Dried the combined organic portions with sodium sulfate (anh.) and removed the solvent in vacuo. Added toluene and heated to reflux for 18 h. Removal of the solvent in vacuo followed by trituration with hexane/ether gave unreacted starting material 8 (4.63 g). Concentration of the filtrate in vacuo followed by flash column chromatography (hexane:ethyl acetate 80:20) gave 9 as a yellow solid (12.0 g, 50.1 mmol, 55.1%)

後処理

  1. customresulted
  2. customQuenched with ice
  3. extractionAdded sat. sodium bicarbonate and extracted with ethyl acetate (4×)
  4. dry with materialDried the combined organic portions with sodium sulfate (anh.)
  5. customremoved the solvent in vacuo
  6. temperatureAdded toluene and heated
  7. temperatureto reflux for 18 h
  8. customRemoval of the solvent in vacuo
  9. customgave unreacted

出典と根拠

ORDレコード
ord-cf21ac35805146e3b41953ae232bb7fa
出典データセット
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06870055B2

反応ノート

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