Potassium Carbonate → Methyl 5-(3-tert-butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylate

HRID 534834

Reaktionsgleichung

Reaktionsgleichung von HRID 534834
[C:1]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=O.C([O-])([O-])=O.[K+].[K+].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[N+:36]([CH2:38][C:39]([O:41][CH3:42])=[O:40])#[C-:37]>CN(C=O)C>[C:9]([O:8][C:1](=[O:7])[CH2:2][CH2:3][C:4]1[O:6][CH:37]=[N:36][C:38]=1[C:39]([O:41][CH3:42])=[O:40])([CH3:12])([CH3:11])[CH3:10]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 199401P,P-Diphenylphosphinic azideHCID 547815Methyl isocyanoacetateHCID 22317022Butanedioic acid,1-(1,1-dimethylethyl) ester

Produkt 1

HCID 66750859Methyl 5-(3-tert-butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylateAusbeute 84,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To an ice-cooled mixture of mono-tert-butyl succinate (5.0 g, 28.7 mmol) and K2CO3 (15.9 g, 114.8 mmol) in DMF (40 mL) were added diphenylphosphoryl azide (11.06 g, 40.2 mmol) and methyl isocyanoacetate (3.41 g, 34.4 mmol). After being stirred at room temperature for 16 h, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica-gel, 9:1-3:7 hexane/ethyl acetate) to give the title compound (6.20 g) as a brown oil.

Aufarbeitung

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by flash column chromatography (silica-gel, 9:1-3:7 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f59a35e893d049e8a056d551c7844101
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853215B2

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