Oxazole → HCID 22293929, compound
Reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[Cl:11][CH2:12][CH2:13][C:14](Cl)=[O:15].[Cl-].[NH4+]>O1CCCC1.[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C>[Cl:11][CH2:12][CH2:13][C:14]([C:2]1[O:1][CH:5]=[CH:4][N:3]=1)=[O:15]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of oxazole (2.93 g, 42.5 mmol) in tetrahydrofuran (150 ml) at −70° C. under a nitrogen atmosphere was added n-butyllithium (2.5 M solution in hexanes, 17 ml) dropwise and the solution stirred for 20 minutes. Zinc chloride (1 M solution in diethyl ether, 84.9 ml) was added and the solution warmed to 0° C. over 45 minutes. Solid cuprous iodide (8.09 g, 42.5 mmol) was added and after 10 minutes, 3-chloropropionyl chloride (8.38 ml, 87.8 mmol) was added. After 1 h, ethyl acetate and aqueous ammonium chloride solution were added. The organic layer was separated and washed sequentially with aqueous ammonium chloride solution, water and brine. The solution was dried (sodium sulphate) and evaporated to yield the crude product as a red oil (15.5 g). This material was used without further purification.
Workup
- waitAfter 1 h
- customThe organic layer was separated
- washwashed sequentially with aqueous ammonium chloride solution, water and brine
- dry with materialThe solution was dried (sodium sulphate)
- customevaporated
Sources & evidence
- ORD record
- ord-e4a3f07fe68745e2bf84435e866c0918
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06953797B2
Reaction notes
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