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

HRID 534834Notes

Reaction equation

HRID 534834 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 66750859Methyl 5-(3-tert-butoxy-3-oxopropyl)-1,3-oxazole-4-carboxylateYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f59a35e893d049e8a056d551c7844101
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

Loading…