Sodium Sulfite → HCID 66643629, compound
Reaction equation
[CH2:1]([O:5][C:6]1[CH:10]=[C:9]([CH3:11])[O:8][N:7]=1)[CH:2]([CH3:4])[CH3:3].[I:12]Cl.S([O-])([O-])=O.[Na+].[Na+]>CC(O)=O.O>[I:12][C:10]1[C:6]([O:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[N:7][O:8][C:9]=1[CH3:11]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 3-isobutoxy-5-methyl-isoxazole (570 mg, 3.67 mmol) in AcOH (15 mL) and water (18 mL) at ambient temperature was added ICl (716 mg, 4.40 mmol) and the reaction mixture heated at 80° C. After 2 h the reaction mixture was cooled to room temperature. After 14 h, a solution of sodium sulfite (Na2SO3, 1 g) in water (15 mL) was added and the reaction mixture extracted into ethyl acetate (2×50 mL). The combined extracts were washed with water (3×30 ml) and brine then dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, 0-10% ethyl acetate in heptane) gave the title compound (706 mg, 68%) as a colourless liquid.
Workup
- temperatureAfter 2 h the reaction mixture was cooled to room temperature
- extractionthe reaction mixture extracted into ethyl acetate (2×50 mL)
- washThe combined extracts were washed with water (3×30 ml) and brine
- dry with materialthen dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customPurification by chromatography (silica, 0-10% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-ef662d4afeb249b09c5a78eee9d25959
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357703B2
Reaction notes
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