Diethyl Ether → 5-Nitrofuroyl chloride

HRID 838870

Reaction equation

HRID 838870 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S1C=CC=C1[Cl:17].CCOCC>CN(C)C=O>[N+:1]([C:4]1[O:8][C:7]([C:9]([Cl:17])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 72992-ChlorothiopheneHCID 125775-Nitro-2-Furoic Acid

Product 1

HCID 907115-Nitrofuroyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3.00 g. of 5-nitro-2-furan-carboxylic acid and 2.06 ml. of thienyl chloride in 50 ml. ether is added 0.45 ml. of dimethyl formamide. The reaction mixture is stirred overnight, under nitrogen, at room temperature. The ether solution is then decanted and the solvent removed to yield 5-nitro-2-furancarboxylic acid chloride, which is then dissolved in 50 ml. ether at 0° . To this solution is added, under nitrogen, 2.06 g. of cyclopropanemethyl alcohol and 3.1 of pyridine. The reaction mixture is allowed to warm to room temperature and is stirred for six days. Ether and water is added to the reaction mixture, the ether layer is decanted, and the aqueous phase is extracted once with ether. The combined organic phases are washed with 2N sulfuric acid, sodium carbonate, water, saturated copper sulfate, and brine, dried over calcium sulfate and the solvent removed to give 3.36 g. of cyclopropanemethyl 5-nitro-2-furancarboxylate, melting point 78°-80°.

Workup

  1. additionTo a mixture of 3.00 g
  2. customThe ether solution is then decanted
  3. customthe solvent removed

Sources & evidence

ORD record
ord-96b86ab329b24e9cb327f6e7b6ab7f2e
Source dataset
uspto-grants-1978_06
Patent number
US04093622

Linked notes

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