Chloroform → Ethyl 5-butoxy-1,3-oxazole-2-carboxylate
Reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:15]([O:17][C:18](=[O:30])[C:19]([NH:21][CH2:22][C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])=O)[CH3:16].CCOC(C)=O.C(Cl)(Cl)Cl>CC#N.[Cl-].[Na+].O>[CH2:26]([O:25][C:23]1[O:24][C:19]([C:18]([O:17][CH2:15][CH3:16])=[O:30])=[N:21][CH:22]=1)[CH2:27][CH2:28][CH3:29]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A suspension of P2O5 (22 g, 155.6 mmol) in CH3CN (50 mL) under nitrogen was warmed to 50° C. and treated with butyl N-[ethoxy(oxo)acetyl]glycinate (6 g, 25.9 mmol) dissolved in 10 mL CH3CN. The mixture was heated to 65° C. for 1.5 hours, then cooled in an ice bath. Ice and brine were added to the reaction mixture, then EtOAc was added and the mixture transferred to a separatory funnel. CHCl3 was added to dissolve solids and the organic layer was isolated. The aqueous layer was washed repeatedly with CHCl3 and EtOAc, the organic layers were combined and dried with Na2SO4, then concentrated. The residue was chromatographed on silica eluting with a gradient of 0-30% EtOAc/Hexanes to give the product as a clear, colorless oil.
Workup
- temperatureThe mixture was heated to 65° C. for 1.5 hours
- temperaturecooled in an ice bath
- customthe mixture transferred to a separatory funnel
- dissolutionto dissolve solids
- customthe organic layer was isolated
- washThe aqueous layer was washed repeatedly with CHCl3 and EtOAc
- dry with materialdried with Na2SO4
- concentrationconcentrated
- customThe residue was chromatographed on silica eluting with a gradient of 0-30% EtOAc/Hexanes
- customto give the product as a clear, colorless oil
Sources & evidence
- ORD record
- ord-f2dc169bf52842899053df8afcd8fa41
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598264B2
Reaction notes
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