Water → 2-(2-Methyl-1,3-oxazol-5-yl)acetonitrile
Reaction equation
Br[CH2:2][C:3]1[O:7][C:6]([CH3:8])=[N:5][CH:4]=1.[C-:9]#[N:10].[Na+].O>CN(C=O)C>[CH3:8][C:6]1[O:7][C:3]([CH2:2][C:9]#[N:10])=[CH:4][N:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution of 5-(bromomethyl)-2-methyl-oxazole CAS [82190-68-9] (15 g, 85 mmol) in DMF (150 mL) was treated with NaCN (10.4 g, 213 mmol) at room temperature and the mixture stirred at 70° C. for 1 h. After this time the mixture was poured onto ice-cooled water (300 mL) and extracted with CH2Cl2 (5×200 mL). The combined organic extracts were then washed with brine, dried with Na2SO4 for 30 min, and the mixture concentrated to afford crude 2-methyl-5-oxazoleacetonitrile product CAS [1159511-94-0] (10 g).
Workup
- additionAfter this time the mixture was poured onto ice-
- extractionextracted with CH2Cl2 (5×200 mL)
- washThe combined organic extracts were then washed with brine
- dry with materialdried with Na2SO4 for 30 min
- concentrationthe mixture concentrated
Sources & evidence
- ORD record
- ord-1cbcc4579cd64f388e091033012f9d46
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927546B2
Reaction notes
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