Phenylacetaldehyde → t-Butyl 4-phenyl-2-butenoate

HRID 1107111Notes

Reaction equation

HRID 1107111 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7]P(OCC)(OCC)=O)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:19]1([CH2:25][CH:26]=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[C:19]1([CH2:25][CH:26]=[CH:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:16])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 998PhenylacetaldehydeHCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 53401901t-Butyl 4-phenyl-2-butenoateYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 12.15 mL (45.78 mmol) of t-butyldiethylphosphonoacetate in 100 mL of THF under argon at 25° C. is added 1.83 g (45.78 mmol) of 60% NaH in oil dispersion. The reaction mixture is stirred at 25° C. for 45 minutes at which time 5.41 mL (41.62 mmol) of phenylacetaldehyde is added. After 30 minutes at 25° C. the reaction is partitioned between 1 N HCl and ethyl ether. The organic layer is dried over anhydrous MgSO4 and concentrated in vacuo. Purification by flash silica gel chromatography affords 6.3 g (69%) of t-butyl 4-phenylbut-2-enoate as a yellow oil.

Workup

  1. additionis added
  2. customAfter 30 minutes at 25° C. the reaction is partitioned between 1 N HCl and ethyl ether
  3. dry with materialThe organic layer is dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-722fdd3a62bc411a9afdc5a2f5fc55d0
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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