Water → tert-butyl 3-[(1E)-3-(benzyloxy)-3-oxopropa-1-en-1-yl]benzoate

HRID 1497552Notes

Reaction equation

HRID 1497552 reaction equation
COP([CH2:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])(=O)OC.[H-].[Na+].[CH:20]([C:22]1[CH:23]=[C:24]([CH:32]=[CH:33][CH:34]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=O.O>O1CCCC1.C(OCC)(=O)C>[CH2:11]([O:10][C:8](=[O:9])/[CH:7]=[CH:20]/[C:22]1[CH:23]=[C:24]([CH:32]=[CH:33][CH:34]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2773759Benzyl DimethylphosphonoacetateHCID 10845940Tert-butyl 3-formylbenzoate

Product 1

HCID 90281965tert-butyl 3-[(1E)-3-(benzyloxy)-3-oxopropa-1-en-1-yl]benzoateYield 60.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of dimethyl(benzyloxycarbonyl)methylphosphonate (2.20 g) in tetrahydrofuran (32.0 mL) was added 55% sodium hydride (406 mg) under ice-cooling, followed by stirring at room temperature for 30 minutes. Subsequently, tert-butyl 3-formylbenzoate (1.60 g) was added thereto, followed by stirring at room temperature for 16 hours. To the reaction mixture were added water and ethyl acetate, and the organic layer was extracted. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 3-[(1E)-3-(benzyloxy)-3-oxopropa-1-en-1-yl]benzoate (1.60 g).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 16 hours
  3. extractionthe organic layer was extracted
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6844a2212df64ddea1f8b88011d39cd9
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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