Sodium Carbonate → 3-(Isoxazol-4-yl)benzaldehyde

HRID 401175Notes

Reaction equation

HRID 401175 reaction equation
I[C:2]1[CH:3]=[N:4][O:5][CH:6]=1.[CH:7]([C:9]1[CH:10]=[C:11](OB(O)O)[CH:12]=[CH:13][CH:14]=1)=[O:8].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:5]1[CH:6]=[C:2]([C:13]2[CH:14]=[C:9]([CH:10]=[CH:11][CH:12]=2)[CH:7]=[O:8])[CH:3]=[N:4]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 219871053-Formylphenyl dihydrogen borateHCID 222740604-Iodo-1,2-oxazole

Product 1

HCID 834815113-(Isoxazol-4-yl)benzaldehydeYield 1.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21931398DME H2O Toluene EtOHSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-iodoisoxazole (1 g, 5.13 mmol), 3-formylphenylboric acid (923 mg, 6.15 mmol) and sodium carbonate in DME/H2O/Toluene/EtOH (15 mL, 3/1/10/6, V/V) was added Pd(PPh3)4 (200 mg). The mixture was purged with N2 for 30 min and heated to 80° C. for 3 h. The reaction mixture was cooled followed by a standard aqueous/EtOAc workup and purified by prep-TLC (EA:PE=1:5) to give Intermediate 46 (12 mg, 1.5%).

Workup

  1. customThe mixture was purged with N2 for 30 min
  2. temperatureThe reaction mixture was cooled
  3. custompurified by prep-TLC (EA:PE=1:5)

Sources & evidence

ORD record
ord-f82ef94ab3dc4296957641e71eab89e5
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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