1,4-Dichlorobutane → Methyl acetoacetate

HRID 2351367Notes

Reaction equation

HRID 2351367 reaction equation
[N:1]1C=[C:5]([C:7]([O:9]C)=[O:8])[CH:4]=[C:3]([C:11]([O:13][CH3:14])=[O:12])C=1.[N+:15]([C:18]1[CH:25]=[C:22]([CH:23]=[O:24])[C:21]([OH:26])=[CH:20][CH:19]=1)([O-:17])=[O:16].C(=O)([O-])[O-:28].[K+].[K+].[Cl:33][CH2:34][CH2:35][CH2:36][CH2:37]Cl>C(O)C>[Cl:33][CH2:34][CH2:35][CH2:36][CH2:37][O:26][C:21]1[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:25][C:22]=1[CH:23]=[O:24].[C:11]([O:13][CH3:14])(=[O:12])[CH2:3][C:4]([CH3:5])=[O:28].[C:7]([O-:9])(=[O:8])[CH3:5].[NH4+:1]

Participants

8

Reactant 4

HCID 80591,4-DichlorobutaneHCID 11430Potassium CarbonateHCID 668085-NitrosalicylaldehydeHCID 78339Dimethyl pyridine-3,5-dicarboxylate

Product 3

HCID 7757Methyl acetoacetateHCID 517165Ammonium AcetateHCID 198462802-(4-Chlorobutoxy)-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The dimethyl pyridine-3,5-dicarboxylate (m.p. 204°-206° C.) used as starting material was obtained by a similar process to that described in the second part of Example 3, using 5-nitrosalicylaldehyde (16.7 g.), potassium carbonate (13.8 g.), 1,4-dichlorobutane (25.4 g.) and diemthylformamide (300 ml.) as initial starting materials, and the 2-(4-chlorobutoxy)-5-nitrobenzaldehyde thus obtained (3.0 g., m.p. 51°-52° C.), methyl acetoacetate (2.7 g.), ammonium acetate (1.0 g.) and ethanol (30 ml.) as reactants in the subsequent reaction (the ammonium acetate and part of the methyl acetoacetate being equivalent to methyl 3-aminocrotonate).

Workup

  1. customwas obtained by a similar process to that

Sources & evidence

ORD record
ord-66f3a54dea9440aba38ed54601f61304
Source dataset
uspto-grants-1989_10
Patent number
US04873254

Reaction notes

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