Sodium hydride → t-Butyl 7-phenyl-2-heptenoate

HRID 1107104Notes

Reaction equation

HRID 1107104 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 561886BenzenepentanalHCID 2773685tert-Butyl diethylphosphonoacetate

Product 1

HCID 54541139t-Butyl 7-phenyl-2-heptenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

t-butyl diethylphosphonoacetate (18 g; 70 mmol) is dissolved in dry THF (250 mL) and cooled to -40° C. NaH (60% in oil; 2.8 g; 70 mmol) is added and the reaction is warmed to 0° C. Gas evolution is controlled with cooling and then stirred at 20° C. for 30 minutes. 5-Phenylpentanal (11.3 g; 70 mmol) is added and the reaction stirred 20 minutes. The reaction is concentrated to half volume and petroleum ether (500 mL) is added. The reaction is washed with 100 mL water, 100 mL 0.5 N HCl, NaHCO3, brine and dried (MgSO4). The solution is concentrated in vacuo to obtain t-butyl 7-phenylhept-2-enoate which is used directly in Step C.

Workup

  1. temperaturethe reaction is warmed to 0° C
  2. temperaturewith cooling
  3. stirringthe reaction stirred 20 minutes
  4. concentrationThe reaction is concentrated to half volume and petroleum ether (500 mL)
  5. additionis added
  6. washThe reaction is washed with 100 mL water, 100 mL 0.5 N HCl, NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-3ff9e7fb628447f18a01611bfbf64ddd
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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