Malonic Acid → (2E)-3-(5-BROMO(2-THIENYL))PROP-2-ENOIC ACID

HRID 549280Notes

Reaction equation

HRID 549280 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[Br:8][C:9]1[S:13][C:12](C=O)=[CH:11][CH:10]=1.N1CCCCC1>N1C=CC=CC=1>[Br:8][C:9]1[S:13][C:12](/[CH:1]=[CH:2]/[C:3]([OH:5])=[O:4])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 2059999(2E)-3-(5-BROMO(2-THIENYL))PROP-2-ENOIC ACID

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Malonic acid (44.40 g, 426.7 mmol) was added to a mixture of 5-bromothiophene-2-carbaldehyde (50 g, 261.7 mmol), piperidine (2.84 mL) and pyridine (150 mL). The mixture was refluxed for 1 h at 80° C. and than at 100° C. over night. The volatiles were evaporated and the residue was dissolved in water and acidified with hydrochloric acid (pH 2). The crude product was crystallized in ethanol. Yield: 55.24 g (90.5%). 1H NMR (270 MHz, CH3OH-d4) δ ppm 6.14 (d, J=15.83 Hz, 1H) 7.11-7.16 (m, 2H) 7.68 (d, J=16.36 Hz, 1H); MS 233.1 (M−H)+; Purity (HPLC) 94%.

Workup

  1. customThe volatiles were evaporated
  2. dissolutionthe residue was dissolved in water
  3. customThe crude product was crystallized in ethanol

Sources & evidence

ORD record
ord-4fa273bc683840b1afd4a18cf9d455e1
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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