Propargyl bromide → HCID 86632584, compound
Reaction equation
[S:1]1([CH2:7][CH2:6][CH2:5][CH2:4]1)(=[O:3])=[O:2].[CH2:8]([Li])[CH2:9][CH2:10]C.C(Br)C#C>C1COCC1>[CH2:10]([CH:4]1[CH2:5][CH2:6][CH2:7][S:1]1(=[O:3])=[O:2])[C:9]#[CH:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of sulfolane (1.0 g, 8.32 mmol) in THF (5 mL) at −78° C. is added n-butyllithium (5.7 mL of 1.6 M in hexane, 9.1 mmol) dropwise and the solution is stirred at −78° C. for 20 min. To this is added a solution of propargyl bromide (992 mg, 8.34 mmol) in THF (5 mL) dropwise and the mixture is allowed to warm to RT overnight. The mixture is quenched with 1N HCl and extracted with EtOAc. The organic phase is dried over magnesium sulfate and the solvent removed under reduced pressure. The residue is purified by flash chromatography using hexane/EtOAc (6:4) as eluent to give the title compound.
Workup
- temperatureto warm to RT overnight
- customThe mixture is quenched with 1N HCl
- extractionextracted with EtOAc
- dry with materialThe organic phase is dried over magnesium sulfate
- customthe solvent removed under reduced pressure
- customThe residue is purified by flash chromatography
Sources & evidence
- ORD record
- ord-7e134683eb1a404fa91905b7aed6e408
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084448B2
Reaction notes
Loading…