Water → ethyl (E)-4,4-dimethyl-5-phenyl-2-pentenoate

HRID 1610655Notes

Reaction equation

HRID 1610655 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][C:18]([CH3:28])([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:19]=O.O>C1(C)C=CC=CC=1>[CH3:19][C:18]([CH3:28])([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)/[CH:17]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 70520Benzenepropanal, alpha,alpha-dimethyl-

Product 1

HCID 57446329ethyl (E)-4,4-dimethyl-5-phenyl-2-pentenoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A suspension (17.8 g, 445 mmol) of 60% sodium hydride in liquid paraffin was suspended in toluene (300 ml), and a solution of ethyl diethylphosphonoacetate (99.8 g, 445 mmol) in toluene (50 ml) was added at room temperature. The mixture was stirred for 30 min. A solution of 2,2-dimethyl-3-phenylpropanal (see Tetrahedron Lett., 1273-1275 (1973)) (60.16 g, 370.8 mmol) in toluene (50 ml) was dropwise added, and the mixture was stirred at room temperature for 2 hrs. The reaction solution was poured into water, and the mixture was extracted twice with diethyl ether. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=20/1-9/1) to give the objective substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. extractionthe mixture was extracted twice with diethyl ether
  3. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained crude product
  6. customwas purified by silica gel column chromatography (hexane/ethyl acetate=20/1-9/1)
  7. customto give the objective substance

Sources & evidence

ORD record
ord-bf33ba422cb54415b07bffa055fe1740
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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