Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester → Ethyl 2-(4-methoxybenzoyl)-3-(1,3-benzodioxol-5-yl)-4-nitro-butanoate

HRID 1272533Notes

Reaction equation

HRID 1272533 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]=[CH:11][N+:12]([O-:14])=[O:13])=[CH:4][C:3]=2[O:2]1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=1.N12CCCN=C1CCCCC2>C(OCC)(=O)C>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([CH:24]([CH:10]([C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)[CH2:11][N+:12]([O-:14])=[O:13])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:30])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl esterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 949455-(2-Nitroethenyl)-1,3-benzodioxole

Product 1

HCID 10811775Ethyl 2-(4-methoxybenzoyl)-3-(1,3-benzodioxol-5-yl)-4-nitro-butanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Into a 45-L stirred reactor at ambient temperature were charged 5.819 kg (30.1 moles) 3,4-methylenedioxy-1-(2-nitroethenyl)-benzene and 24 L ethyl acetate. A solution of 5.355 kg (24.1 moles) ethyl 3-(4-methoxyphenyl)-3-oxopropionate in 16 L ethyl acetate was added. 280 g (275 ml, 1.84 moles) of 1,8-diaza-bicyclo[5.4.0]undec-7-ene in four equal portions was added over a 2.5 hour period. The reaction mixture was filtered through dicalite and the resulting filtered solution was used in the next step without any further purification.

Workup

  1. filtrationThe reaction mixture was filtered through dicalite
  2. filtrationthe resulting filtered solution
  3. customwas used in the next step without any further purification

Sources & evidence

ORD record
ord-2215e3cb3d3f44aca0ab28d21cdf7eae
Source dataset
uspto-grants-2007_04
Patent number
US07208517B1

Reaction notes

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