Dimethylformamide → Ethyl 3,3-dicarbethoxy-4-(2-nitro-6-methylphenyl)butyrate

HRID 1283116Notes

Reaction equation

HRID 1283116 reaction equation
[CH:1]([C:13]([O:15][CH2:16][CH3:17])=[O:14])([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[N+:20]([C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:24]=1[CH2:25]Cl)([O-:22])=[O:21].CN(C)C=O>C1C=CC=CC=1>[C:8]([C:1]([C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH2:25][C:24]1[C:27]([CH3:31])=[CH:28][CH:29]=[CH:30][C:23]=1[N+:20]([O-:22])=[O:21])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 81961Triethyl ethane-1,1,2-tricarboxylateHCID 122040702-(chloromethyl)-1-methyl-3-nitroBenzene

Product 1

HCID 21519363Ethyl 3,3-dicarbethoxy-4-(2-nitro-6-methylphenyl)butyrate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The title compound was prepared by the same procedure as described in example 1 for 1a (R2 = R3 = H), using triethyl 1,1,2-ethanetricarboxylate (9.85 g; 0.04 mole), NaH (1.6 g; 0.04 mole) and 2-nitro-6-methylbenzyl chloride (7.4 g; 0.04 mole) in 20 ml. 10% dimethylformamide (DMF) in benzene. The crude product so obtained was used directly in the next step without further purification.

Sources & evidence

ORD record
ord-75996b25040147648f413caddf8a64a0
Source dataset
uspto-grants-1976_08
Patent number
US03974165

Reaction notes

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