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

HRID 2249671Notes

Reaction equation

HRID 2249671 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 68983960Ethyl 3-(2-isobutoxyphenyl)-2-propenoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

In 30 ml of tetrahydrofuran is suspended 0.92 g of 60% sodium hydride. After dropping 5.0 ml of ethyl diethylphosphonoacetate thereinto at ambient temperature over a period of 5 minutes, the mixture thus obtained is stirred at 40° C. for 30 minutes. Then, a solution of 3.40 g of 2-isobutoxybenzaldehyde in 20 ml of tetrahydrofuran is dropwise added at ambient temperature over a period of 20 minutes, and the mixture thus obtained is stirred for one hour. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to obtain 4.30 g of ethyl 3-(2-isobutoxyphenyl)-2-propenoate as a light yellow oily product.

Workup

  1. customthe mixture thus obtained
  2. customthe mixture thus obtained
  3. stirringis stirred for one hour
  4. customthe organic layer is separated
  5. customThe organic layer thus obtained
  6. washis washed with water and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. customThe residue thus obtained
  10. customis purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-bd1a93d8e8914827a2526eb9400828ab
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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