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

HRID 7361

Reaction equation

HRID 7361 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6e4a81ed99724d89ab0593aba47b36bc
Source dataset
uspto-grants-2006_08
Patent number
US07087579B2

Linked notes

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