Sodium hydride → HCID 67543258, compound

HRID 872012Notes

Reaction equation

HRID 872012 reaction equation
C(OP([CH:9]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[F:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O>O1CCCC1>[F:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)/[CH:29]=[C:9](\[CH2:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680093-FluorobenzaldehydeHCID 11121291HCID 11121291, compound

Product 1

HCID 67543258HCID 67543258, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-tert-butyl 1-ethyl 2-(diethoxyphosphoryl)succinate (28.60 g) in tetrahydrofuran (70 ml) was added dropwise to a suspension of 60% oily sodium hydride (3.39 g) in tetrahydrofuran (100 ml) under ice-cooling during 20 minutes, the mixture was stirred at the same temperature for an hour. Next, a solution of 3-fluorobenzaldehyde (10.00 g) in tetrahydrofuran (30 ml) was added thereto and the mixture was stirred at room temperature for 3 hours. Ice-water was added to the reaction mixture under ice-cooling and it was extracted with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over sodium sulfate and concentrated in vacuo to give 4-tert-butyl 1-ethyl(2E)-2-(3-fluorobenzylidene)succinate (27.7 g) as a crude yellow oil.

Workup

  1. temperaturecooling during 20 minutes
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. temperaturecooling
  4. extractionit was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine successively
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6eded7e904ef436cbfa4ce274f28af84
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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