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 solution. The suspension was filtered through glass fiber filter paper, washing with ethyl acetate. The filtrate was washed with saturated sodium bicarbonate solution and 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 (0.992 g, 47%). 400 M Hz 1H-NMR (CDCl3) δ: 5.80 (ddd, J=15.6 Hz, 4.1 Hz and 2.3 Hz, 1H), 5.66 (ddd, J=15.6 Hz, 4.1 Hz and 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 solution
- filtrationThe suspension was filtered through glass fiber
- filtrationfilter paper
- washwashing with ethyl acetate
- washThe filtrate was washed with saturated sodium bicarbonate solution and brine
- 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-564fe58aed6c4e0ca9b7e681960effb1
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501770B2
Reaction notes
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