Formaldehyde → HCID 17842393, compound

HRID 546400Notes

Reaction equation

HRID 546400 reaction equation
C=O.[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][C:13]1[N:14]=[C:15](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:16][CH:17]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:26](OCC)(=O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][C:13]2[N:14]=[C:15](/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:16][C:17]=2[CH2:26]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22710974HCID 22710974, compound

Product 1

HCID 17842393HCID 17842393, compound

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

Paraformaldehyde (54.5 mg) and p-toluenesulfonic acid (7.2 mg) were added to a solution of 4-[2-(tert-butoxycarbonylamino)ethyl]-2-(trans-styryl)oxazole (190 mg) in toluene (15 ml) at room temperature. After heating under reflux for 1 hour, the reaction mixture was allowed to cool, and ethyl acetate (15 ml) and a saturated aqueous solution (15 ml) of sodium hydrogen-carbonate were added to the reaction mixture to separate an organic layer. After the water layer was extracted with ethyl acetate (10 ml), the resultant organic layers were combined and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1→2:1) to obtain the title compound (153 mg) as a colorless oil.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 1 hour
  3. temperatureto cool
  4. customto separate an organic layer
  5. extractionAfter the water layer was extracted with ethyl acetate (10 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1→2:1)

Sources & evidence

ORD record
ord-415a5f02ae474cfc8fbd1bd9b6f2a966
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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