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

HRID 1714455Notes

Reaction equation

HRID 1714455 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-583533c564684d6ab3f7a37c919c3534
Source dataset
uspto-grants-2010_09
Patent number
US07795440B2

Reaction notes

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