Malonic Acid → 3-Thiophen-2-ylprop-2-enoic acid

HRID 460360

Reaction equation

HRID 460360 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.C(O)(=O)[CH2:9][C:10]([OH:12])=[O:11].C([O-])(=O)C.[NH4+]>CN(C=O)C.C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:9][C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 867Malonic AcidHCID 73642-Thiophenecarboxaldehyde2×HCID 517165Ammonium Acetate

Product 1

HCID 928683-Thiophen-2-ylprop-2-enoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of thiophene-2-carbaldehyde (Compound 66a) (1.20 g, 0.0107 mol), malonic acid (1.11 g, 0.0107 mol) and ammonium acetate (0.825 g, 0.0107 mol) in DMF (8.5 mL) was heated to 100° C. for 3 h. The system was diluted with ethyl acetate and washed with water and dried over MgSO4. The solvent was removed in vacuo and the title compound was purified by silica gel column chromatography using 3:1 Hexanes:ethyl acetate as the eluent.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customthe title compound was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dc6b503372ff491c9ba7d69950f12636
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Linked notes

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