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

HRID 993423Notes

Reaction equation

HRID 993423 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CCCCCC.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20]>C(#N)C.O1CCCC1>[CH2:23]([O:22][C:19](=[O:21])[CH:20]=[CH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH3:24]

Participants

5

Reactant 2

HCID 61951-NaphthaldehydeHCID 21226206Ethyl acetate hexane

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

22.4 g (0.10 mol) of triethylphosphonoacetate was dissolved in 500 M of acetonitrile and 30.4 g (0.2 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene(1,5-5)(DBU) 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 and the mixture was stirred for 8 hours. The organic solvent was removed by distillation under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed twice with water, dried over magnesium sulfate, concentrated and then 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. customThe organic solvent was removed by distillation under reduced pressure
  2. dissolutionThe resulting 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-c04aa2de74c64bf483385dbfcda16962
Source dataset
uspto-grants-2002_10
Patent number
US06472526B1

Reaction notes

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