1-Naphthaldehyde → Ethyl 3-(naphthalen-1-yl)prop-2-enoate

HRID 1387318Notes

Reaction equation

HRID 1387318 reaction equation
CC(C)([O-])C.[K+].[C:7]1([CH:17]=O)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.CCCCCC.[C:25]([O:28][CH2:29][CH3:30])(=[O:27])[CH3:26]>O1CCCC1>[CH2:29]([O:28][C:25](=[O:27])[CH:26]=[CH:17][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH3:30]

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 53428571Ethyl 3-(naphthalen-1-yl)prop-2-enoateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

22.4 g(0.10 mol) of triethylphosphonoacetate was dissolved in 500 ml of tetrahydrofuran and 12.4 g(1.1 mol) of potassium t-butoxide was slowly added thereto. To this solution was slowly added 15.6 g(0.10 mol) of 1-naphtaldehyde dissolved in 20 ml of tetrahydrofuran and the mixture was stirred for 8 hours. The organic solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate, washed twice with water, dried over anhydrous magnesium sulfate, concentrated and subjected to column chromatography(eluent: hexane/ethyl acetate=95/5, v/v) to give 20.3 g(0.090 mol, Yield 90%) of the title compound.

Workup

  1. customThe organic solvent was removed by distillation under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed twice with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d2d4c5c584074eb287ac9933ae25fd78
Source dataset
uspto-grants-2001_07
Patent number
US06268363B1

Reaction notes

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