HCID 18617480, compound → HCID 18617845, compound

HRID 1264213Notes

Reaction equation

HRID 1264213 reaction equation
[O:1]1C=CC=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])([CH3:16])[C:13]([NH2:15])=[O:14])=[CH:8][CH:7]=1.CC#N.C(Cl)(Cl)(Cl)Cl.[OH2:26]>C(OCC)(=O)C>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])([CH3:16])[C:13]([NH2:15])=[O:14])=[CH:8][CH:7]=1)([OH:1])=[O:26]

Participants

4

Reactant 2

HCID 18617480HCID 18617480, compoundHCID 22592919water acetonitrile CCl4

Product 1

HCID 18617845HCID 18617845, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-(furan-2-yl)-phenyl)-2-methyl-propionamide (reference example 26) (124 mg, 0.5 mmol) in CH3CN/CCl4/H2O (7 mL, 2/2/3) is added NaIO4 (420 mg, 2 mmol) followed by RuCl3 (H2O)(3 mg). The resulting mixture is stirred vigorously for 1.5 h, then diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated to give 100 mg of the title compound as an orange solid. 1H NMR (CD3OD) d 1.58 (s, 6H), 7.50 (d, J=8 Hz, 2H), 7.98 (d, J=8 Hz, 2H). MS (EI) m/z 208 (M+H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0de5536d44ec4a26ab90c97a182724fb
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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