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>[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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 2-methyl-2-propanesulfinamide (1.47 g) and 3-oxetanone (0.85 mL) in THF (24 mL) was added Ti(OEt)4 (5.34 mL) dropwise over the course of 15 minutes at room temperature. After being stirred at 60° C. for 18 h, the reaction mixture was quenched by the rapid addition into ice cooled saturated sodium bicarbonate aqueous solution. The suspension was filtered through glass fiber filter paper and the cake was washed with ethyl acetate. The filtrate was washed with saturated sodium bicarbonate solution then brine. The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (10-100% ethyl acetate in hexanes) gave the product (1.02 g, 48%). 1HNMR (CDCl3) 400 MHz δ: 5.80 (ddd, J=15.6, 4.1, 2.3 Hz, 1H), 5.66 (ddd, J=15.6, 4.1, 2.3 Hz, 1H), 5.52-5.41 (m, 2H), 1.27 (s, 9H).
Workup
- customthe reaction mixture was quenched by the rapid addition into ice cooled saturated sodium bicarbonate aqueous solution
- filtrationThe suspension was filtered through glass fiber
- filtrationfilter paper
- washthe cake was washed with ethyl acetate
- washThe filtrate was washed with saturated sodium bicarbonate solution
- dry with materialThe organics were dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customPurification by column chromatography (10-100% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-0835c2a9e58d4463bc8d3a2418ed3232
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569331B2
Reaction notes
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