tert-Butanol → tert-Butyl ethynsulfonate
Reaction equation
[C:1]([Mg]Cl)#[CH:2].[S:5](Cl)(Cl)(=[O:7])=[O:6].[C:10]([OH:14])([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C1COCC1>[C:1]([S:5]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:7])=[O:6])#[CH:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of ethynylmagnesium chloride in THF (0.5M, 10 mmol) is added to a solution of sulfuryl chloride (20 mmol) in 100 mL of THF cooled to −78° C. After 1 hour, a solution of tert-butanol (60 mmol) and triethylamine (60 mmol) in 50 mL of THF is added dropwise. The solution is allowed to warm to room temperature, the volatile components are evaporated in vacuo, the residue is partitioned between ether (150 mL) and 0.05M HCl (50 mL), the organic phase is washed with brine (50 mL) and dried over MgSO4, and the volatile components are evaporated in vacuo. The residue is purified by flash chromatography to give the product as a colorless oil.
Workup
- temperatureto warm to room temperature
- customthe volatile components are evaporated in vacuo
- customthe residue is partitioned between ether (150 mL) and 0.05M HCl (50 mL)
- washthe organic phase is washed with brine (50 mL)
- dry with materialdried over MgSO4
- customthe volatile components are evaporated in vacuo
- customThe residue is purified by flash chromatography
Sources & evidence
- ORD record
- ord-caa73814f0a64634b30268e42213101f
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06702705B1
Reaction notes
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