Reaction equation
O1CCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:16]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][CH:18]([CH3:20])[CH3:19].FC(F)(F)S(O[Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])(=O)=O>CN1CCCN(C)C1=O>[CH2:23]([O:22][C:16]([O:21][Si:31]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])=[CH:17][CH:18]([CH3:20])[CH3:19])[CH3:24]Participants
Conditions
- Temperature
- -70 °C
Procedure
Tetrahydrofuran (100 ml) and 1,3-dimethyl-3,4,5,6-tetrahydro 2 (1H)-pyrimidinone (140 ml) were mixed at −20° C. and lithium bis (trimethylsilyl) amide (1M in tetrahydrofuran, 100 ml) was added. The mixture was cooled to −70° C., ethyl isovalerate (18.75 ml) added and stirred for ½ hour at −70° C. Triisopropylsilyl trifluoromethane sulfonate was added and the mixture left to stir at −75° C. for ½ hour before warming to room temperature and stirring for 3 hours. The reaction mixture was quenched with aqueous sodium bicarbonate (8%, 150 ml) and extracted with hexane (1000 ml). The hexane extract was washed with water (4×500 ml), dried (MgSO4), filtered and concentrated in vacuo to afford a crude yellow oil containing the title compound.
Workup
- waitthe mixture left
- stirringto stir at −75° C. for ½ hour
- temperaturebefore warming to room temperature
- stirringstirring for 3 hours
- customThe reaction mixture was quenched with aqueous sodium bicarbonate (8%, 150 ml)
- extractionextracted with hexane (1000 ml)
- extractionThe hexane extract
- washwas washed with water (4×500 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto afford a crude yellow oil
Sources & evidence
- ORD record
- ord-7bdf0bcac9b34bd9a369e584d6237570
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06215002B1
Linked notes
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