Hexane → 5,5,5-Trifluoro-1-pentynyl-tri(n-butyl)stannane
Reaction equation
Br[C:2](Br)=[CH:3][CH2:4][CH2:5][C:6]([F:9])([F:8])[F:7].[Li]CCCC.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].CCCCCC>O1CCCC1>[F:7][C:6]([F:9])([F:8])[CH2:5][CH2:4][C:3]#[C:2][Sn:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a −78° C. solution the product from Step A (0.935 mg, 3.31 mmol) in 10 mL of tetrahydrofuran was added n-BuLi solution (2.65 mL, 6.63 mmol, 2.5 M hexanes) dropwise. The reaction was stirred at −78° C. for one hour, then allowed to warm to room temperature for one hour. The solution was cooled to 0° C., and tributyltin chloride (0.898 mL, 3.31 mmol) was added. After 10 minutes, the solution was poured into hexane, washed with saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a brown liquid which was used without further purification.
Workup
- temperatureto warm to room temperature for one hour
- temperatureThe solution was cooled to 0° C.
- waitAfter 10 minutes
- washwashed with saturated NaHCO3 solution and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe product was isolated as a brown liquid which
- customwas used without further purification
Sources & evidence
- ORD record
- ord-4da94bd174aa4d6ab284c7a2bec94def
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562823B1
Reaction notes
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