Acetic Acid → HCID 86588959, compound

HRID 353305Notes

Reaction equation

HRID 353305 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:21].CC(C)([O-])C.[K+].C(O)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[C:23](\[O:22][CH2:20][CH3:21])/[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 69955Ethyl ethoxyacetateHCID 70235544-(Benzyloxy)-3-nitrobenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 86588959HCID 86588959, compoundYield 15.9%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

4-(Benzyloxy)-3-nitrobenzaldehyde (4.12 g; 14.4 mmole) and ethyl ethoxyacetate (2.29 g; 17.3 mmole) were dissolved in dry tetrahydrofuran (20 ml) and cooled to −20° C. Potassium tert-butoxide (1.94 g; 17.3 mmole) dissolved in dry tetrahydrofuran (10 ml) was slowly added and the reaction was stirred overnight at −20° C. The reaction was quenched with acetic acid (1.3 g; 21.7 mmole). The crude product was isolated, redissolved in toluene and refluxed over night with p-toluenesulfonic acid (0.25 g; 1.44 mmole) in a Dean-Stark apparatus to separate the water. The solution was cooled, washed with sodium hydrogen carbonate, dried with magnesium sulfate and evaporated. Chromatography of the crude material from methylene chloride gave 0.85 g (11% yield) of ethyl (2Z)-3-[4-(benzyloxy)-3-nitrophenyl]-2-ethoxyacrylate.

Workup

  1. additionwas slowly added
  2. customThe crude product was isolated
  3. customto separate the water
  4. temperatureThe solution was cooled
  5. washwashed with sodium hydrogen carbonate
  6. dry with materialdried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-9bf7cf013c9346a6ba84e0b6b4b2f77f
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Reaction notes

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