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

HRID 457488

반응식

HRID 457488 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-00664c33b4eb44be867816def077880d
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189702B2

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