Methyl iodide → HCID 10493998, compound
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1C(=O)C[S:8][C:7]1([CH3:13])[CH3:12].I[CH3:15].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:26]1[CH2:30][O:29]C[CH2:27]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:30](=[O:29])[C:26]([CH3:27])([CH3:15])[S:8][C:7]1([CH3:12])[CH3:13]Participants
5
Conditions
- Temperature
- -75 °C
Procedure
To a -75° C. solution of 3-(4-bromobutyl)-2,2-dimethyl-4-thiazolidinone (13.18 g), iodomethane (22.83 g) and THF (30 ml) was added a -75° C. solution of lithium bis(trimethylsilyl)amide (0.100 mol) in THF (110 ml) over a period of 12 minutes. The resulting solution was stirred at -75° C. for 25 minutes, removed from the cold bath and acidified with 1N HCl (250 ml). The aqueous mixture was extracted with diethylether (3×125 ml). The combined extracts were washed with brine (150 ml), dried (anhydrous Na2SO4) and concentrated under reduced pressure to give 16.86 g of liquid. Column chromatography of the liquid using silica gel (about 600 g) and elution with 30% ethyl acetate/hexanes afforded 12.50 g of oil.
Workup
- customremoved from the cold bath
- extractionThe aqueous mixture was extracted with diethylether (3×125 ml)
- washThe combined extracts were washed with brine (150 ml)
- dry with materialdried (anhydrous Na2SO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f20bf66429a045f4a3cca3799be7a999
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05136037
Reaction notes
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