Piperonal → HCID 10679193, compound

HRID 917661Notes

Reaction equation

HRID 917661 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[N+:18]([CH2:20]S(C1C=CC(C)=CC=1)(=O)=O)#[C-:19]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][CH:20]=[N:18][CH:19]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 8438PiperonalHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanide

Product 1

HCID 10679193HCID 10679193, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of benzo[1,3]dioxole-5-carbaldehyde (657 mg, 4.83 mmol) in methanol (15 mL) was added potassium carbonate (786 mg, 5.69 mmol, 1.3 equiv) and 1-isocyanomethanesulfonyl-4-methyl-benzene (863 mg, 4.38 mmol, 1 equiv). The resulting solution was heated to 70° C. under a nitrogen atmosphere for 3 hours, cooled to ambient temperature, and concentrated in vacuo. The residue was partitioned between methylene chloride and water, and the aqueous layer was extracted three times with methylene chloride. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Silica gel chromatography (30% ethyl acetate in hexanes) provided 5-benzo[1,3]dioxol-5-yl-oxazole (676 mg, 82%).

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between methylene chloride and water
  4. extractionthe aqueous layer was extracted three times with methylene chloride
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9185134dfacf4d4c87fec07913a1e7c0
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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