Acetic Acid → HCID 54429179, compound

HRID 396679Notes

Reaction equation

HRID 396679 reaction equation
[C:1]([O:7][CH2:8][CH2:9][C:10]#[N:11])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[O:12]1[C:17]2[CH:18]=[CH:19][C:20]([CH:22]=O)=[CH:21][C:16]=2[O:15][CH2:14][CH2:13]1.N1CCCCC1.C(O)(=O)C>CC(O)C>[C:10]([CH2:9][CH2:8][O:7][C:1](=[O:6])[C:2](=[CH:22][C:20]1[CH:19]=[CH:18][C:17]2[O:12][CH2:13][CH2:14][O:15][C:16]=2[CH:21]=1)[C:3](=[O:4])[CH3:5])#[N:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 123604062-Cyanoethyl 3-oxobutanoate

Product 1

HCID 54429179HCID 54429179, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 2-cyanoethyl acetoacetate (5.00 g, 32.2 mmol), 1,4-benzodioxan-6-carboxaldehyde (5.29 g, 32.2 mmol), piperidine (137 mg, 1.61 mmol) and acetic acid (97 mg, 1.6 mmol) in 70 ml of 2-propanol was stirred at r.t. for 48 hrs. After evaporation of solvent, the product was purified by chromatography (SiO2, AcOEt: Hexane, 60:10). 2-[(3,4-Ethylenedioxyphenyl)methylene]-3-oxobutanoic acid 2-cyanoethyl ester was obtained as a yellowish oil (2.64 g, 27% yield).

Workup

  1. customAfter evaporation of solvent
  2. customthe product was purified by chromatography (SiO2, AcOEt: Hexane, 60:10)

Sources & evidence

ORD record
ord-aa042cc876fb4c92a334d2e1fa2a6309
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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