Ethyl Acetate → ethyl (E)-3-(2-isobutoxyphenyl)-2-propenoate

HRID 501783Notes

Reaction equation

HRID 501783 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:17]([O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=O)[CH:18]([CH3:20])[CH3:19].C(OCC)(=O)C>O1CCCC1.O>[CH2:17]([O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1/[CH:24]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:18]([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 38575282-(2-Methylpropoxy)benzaldehyde

Product 1

HCID 17816555ethyl (E)-3-(2-isobutoxyphenyl)-2-propenoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

0.92 g of 60% sodium hydride was suspended in 30 mL of tetrahydrofuran, to which 5.0 mL of ethyl diethylphosphonoacetate was added dropwise over 5 minutes at room temperature, and this mixture was stirred for 30 minutes at 40° C. Then, after 3.40 g of 2-isobutoxybenzaldehyde dissolved in 20 mL of tetrahydrofuran was added to the mixture dropwise over 20 minutes at room temperature, this mixture was stirred for one hour at the same temperature. The reaction mixture was added to a mixture of ethyl acetate and water, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=9:1] to yield 4.30 g of ethyl (E)-3-(2-isobutoxyphenyl)-2-propenoate as light yellow oil.

Workup

  1. additionwas added dropwise over 5 minutes at room temperature
  2. additionwas added to the mixture dropwise over 20 minutes at room temperature
  3. stirringthis mixture was stirred for one hour at the same temperature
  4. customthe organic phase was separated
  5. washAfter the resultant organic phase was washed with water
  6. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled out under reduced pressure
  8. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=9:1]

Sources & evidence

ORD record
ord-bed8a0197ac0425d8d5f85497bb55ed4
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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