Tert-Butanesulfinamide → 2-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide
Reaction equation
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[O:8]1[CH2:11][C:10](=O)[CH2:9]1>C1COCC1.[Cl-].[Na+].O>[CH3:1][C:2]([S:5]([N:7]=[C:10]1[CH2:11][O:8][CH2:9]1)=[O:6])([CH3:4])[CH3:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
2-Methylpropane-2-sulfinamide (3.36 g, 27.77 mmol, 1 eq) and Ti(OEt)4 (12 ml, 55.54 mmol, 2 eq) were added to a solution of oxetan-3-one (2 g, 27.77 mmol, 1 eq) in THF at 22° C. The reaction mixture was stirred at 50° C. for 5 h. It was cooled to room temperature and poured into saturated brine solution, and then the suspension was filtered through a pad of Cellite. The filtrate was extracted with ethyl acetate, and the organic layer washed with saturated brine solution, dried over Na2SO4 and concentrated. The crude product was purified by silica gel (60-120 mesh) columatography using 30% EtOAc/Petroleum ether. Yield: 0.55 g (45.4%).
Workup
- temperatureIt was cooled to room temperature
- filtrationthe suspension was filtered through a pad of Cellite
- extractionThe filtrate was extracted with ethyl acetate
- washthe organic layer washed with saturated brine solution
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe crude product was purified by silica gel (60-120 mesh) columatography
Sources & evidence
- ORD record
- ord-f2e18a1a779344948eb942a5e07e06fa
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507683B2
Reaction notes
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