Hexane → 4-(1,3-Dioxolan-2-yl)-5-tributylstannylthiazole
Reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)[N:6]=1.C([Li])CCC.CCCCCC.[CH2:23]([Sn:27](Cl)([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26]>C1COCC1.O>[O:8]1[CH2:9][CH2:10][O:11][CH:7]1[C:5]1[N:6]=[CH:2][S:3][C:4]=1[Sn:27]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH3:26]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
2-Bromo-4-(1,3-dioxolan-2-yl)thiazole (6.4 g, 27.14 mmol) was stirred at −78° C. in dry THF (38 ml).1.6M n butyl lithium in hexane (18.6 ml, 29.78 mmol) was added dropwise under nitrogen. After 30 min at this temperature, tributyl tin chloride (7.35 ml, 27.14 mmol) was added dropwise. The reaction was allowed to warm to 0° C. and water (20 ml) was added. The product was extracted into ether (3×100 ml). The combined organic extracts were dried (MgSO4) and evaporated. The residue was triturated with isohexane (3×100 ml) and the mother liquors were decanted, combined and concentrated to give a brown oil (11.88 g); m/z 444-450.
Workup
- extractionThe product was extracted into ether (3×100 ml)
- dry with materialThe combined organic extracts were dried (MgSO4)
- customevaporated
- customThe residue was triturated with isohexane (3×100 ml)
- customthe mother liquors were decanted
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f99d0a26fb8342c5b0441ce45d840f43
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727256B1
Reaction notes
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