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 1 N HCl (250 ml). The aqueous mixture was extracted with diethylether (3x 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 (3x 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-fe70e1583257422aa010b04fdd4fef14
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06284775B1
Reaction notes
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