Propanal → methyl (E)-4-(but-1-en-1-yl)benzoate

HRID 7361

反応式

HRID 7361 の反応式
[H-].[Na+].C(P([CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)(CC)=O)C.[CH:20](=O)[CH2:21][CH3:22].[Cl-].[NH4+]>O1CCCC1>[CH:9](/[C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=1)=[CH:20]\[CH2:21][CH3:22]

参加物

6

反応物 4

HCID 527PropanalHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 21989718Methyl 4-(diethylphosphorylmethyl)benzoate

生成物 1

HCID 12737446methyl (E)-4-(but-1-en-1-yl)benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of sodium hydride (60%, 0.97 g) in tetrahydrofuran (80 mL) was added methyl 4-(diethylphosphorylmethyl)benzoate (5.8 g) at 0° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of propionaldehyde (1.6 mL) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give methyl (E)-4-(but-1-en-1-yl)benzoate (2.5 g).

後処理

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-6e4a81ed99724d89ab0593aba47b36bc
出典データセット
uspto-grants-2006_08
特許番号
US07087579B2

関連ノート

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