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

HRID 1635935Notes

Reaction equation

HRID 1635935 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.[CH2:19]([O:21][C:22](=[O:24])[CH3:23])[CH3:20]>C(#N)C.O1CCCC1.C(OC(=O)C)C>[CH2:19]([O:21][C:22](=[O:24])[CH:23]=[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)[CH3:20]

Participants

6

Reactant 2

HCID 61951-NaphthaldehydeHCID 21226206Ethyl acetate hexane

Product 1

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

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

22.4 g(0.10 mol) of triethylphosphonoacetate was dissolved in 500 ml of acetonitrile and 30.4 g(2mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (1,5-5)(DBU) was slowly added thereto. 15.6 g(0.10 mol) of 1-naphthaldehyde dissolved in 20 ml of tetrahydrofuran was slowly added to the above reaction solution and the resulting mixture was stirred for 8 hours. The organic solvent was removed under reduced pressure, the residue thus obtained was dissolved in ethylacetate, washed twice with water, dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography(eluent: n-hexane/ethylacetate=95/5, v/v) to give 20.3 g(0.090 mol, Yield 90%) of the title compound.

Workup

  1. additionwas slowly added to the above reaction solution
  2. customThe organic solvent was removed under reduced pressure
  3. customthe residue thus obtained
  4. washwashed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ba4adf67592144f288d86c130fc544cd
Source dataset
uspto-grants-2003_01
Patent number
US06511978B1

Reaction notes

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