4-Hydroxy-3-iodobenzaldehyde → HCID 10615412, compound

HRID 1464806Notes

Reaction equation

HRID 1464806 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]#[CH:15].[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=1I>N1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][C:14]1[O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=2[CH:15]=1

Participants

5

Reactant 2

HCID 9688814-Hydroxy-3-iodobenzaldehydeHCID 10535929Oxazole, 5-methyl-2-phenyl-4-(2-propynyl)-

Product 1

HCID 10615412HCID 10615412, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1049PyridineSolvent3×

Procedure

To a slurry of cuprous oxide (12 g, 84 mmol) in pyridine (150 ml) were added a solution of 5-methyl-2-phenyl-4-(2-propynyl)oxazole in pyridine (150 ml) followed by a solution of 4-hydroxy-3-iodobenzaldehyde (35 g, 0.14 mol) in pyridine (100 ml). Bis(triphenylphosphine)palladium (II) chloride (0.50 g, 0.7 mmol) was then added as a solid and the mixture was heated to reflux overnight. The mixture was cooled and concentrated. The residue was taken up in ethyl acetate (250 ml+3×50 ml). The ethyl acetate solution was concentrated and the residue was extracted with hot cyclohexane. The hot solution was filtered and cooled and the solid was collected (29 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. concentrationThe ethyl acetate solution was concentrated
  6. extractionthe residue was extracted with hot cyclohexane
  7. filtrationThe hot solution was filtered
  8. temperaturecooled
  9. customthe solid was collected (29 g)

Sources & evidence

ORD record
ord-0ee98a907a7d4f759405106d7259379a
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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