HCID 72346776, compound → HCID 55283784, compound

HRID 1365752Notes

Reaction equation

HRID 1365752 reaction equation
[CH3:1][S:2][C:3]1[O:7][C:6]([CH:8]=[N:9]O)=[CH:5][CH:4]=1>C(O)(=O)C.[Zn]>[CH3:1][S:2][C:3]1[O:7][C:6]([CH2:8][NH2:9])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 72346776HCID 72346776, compound

Product 1

HCID 55283784HCID 55283784, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 5-(methylthio)furan-2-carbaldehyde oxime (220 mg, 1.40 mmol) in glacial acetic acid (15 mL) was added zinc dust (2.10 g, 32.2 mmol) and the reaction mixture was stirred at 23° C. for 4 h. After filtration on celite, the acetic acid was concentrated in vacuo and the crude material purified on functionalized silica gel (6 g) containing sulfonic acid (0.8 mmol/g) to afford 138 mg (69%) of the title compound as an orange oil. 1H NMR (400 MHz, CDCl3): 6.36 (1H, d, J=3.2 Hz), 6.11 (1H, d, J=3.2 Hz), 3.80 (2H, s), 2.36 (3H, s).

Workup

  1. filtrationAfter filtration on celite
  2. concentrationthe acetic acid was concentrated in vacuo
  3. customthe crude material purified on functionalized silica gel (6 g)
  4. additioncontaining sulfonic acid (0.8 mmol/g)

Sources & evidence

ORD record
ord-16924ff847414adc9be0206849b4db46
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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