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

HRID 2304576Notes

Reaction equation

HRID 2304576 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-naphthaldehyde dissolved in 20 ml of tetrahydrofuran, then the resulting solution was stirred for 8 hours. The organic solvent was eliminated by distillation under reduced pressure, and the residue was dissolved in ethyl acetate, washed twice with water, dried over magnesium sulfate and concentrated. The concentrate was subjected to silica gel column chromatography(eluent: n-hexane/ethyl acetate=95/5, v/v) to obtain 20.3 g(0.090 mol, Yield 90%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-ded08313111e4d859bce1ca4c47e6028
Source dataset
uspto-grants-2002_08
Patent number
US06436960B1

Reaction notes

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