4-Toluenesulfonyl chloride → 8-t-Butyl-3-(p-toluenesulfonyloxy)-1-oxaspiro-(4,5)decane

HRID 232547Notes

Reaction equation

HRID 232547 reaction equation
[C:1]([CH:5]1[CH2:15][CH2:14][C:8]2([O:12][CH2:11][CH:10]([OH:13])[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C1COCC1>[C:1]([CH:5]1[CH2:15][CH2:14][C:8]2([O:12][CH2:11][CH:10]([O:13][S:24]([C:21]3[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=3)(=[O:26])=[O:25])[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 190401578-t-Butyl-3-hydroxy-1-oxaspiro(4,5)decane

Product 1

HCID 190401668-t-Butyl-3-(p-toluenesulfonyloxy)-1-oxaspiro-(4,5)decaneYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8-t-butyl-3-hydroxy-1-oxaspiro(4,5)decane (4.24 g, 20 mmol) in THF (50 ml) was added sodium hydride (0.72 g, 24 mmol, 80% in mineral oil) and the mixture was heated to reflux for 3 hours. p-Toluenesulfonylchloride (4.56 g, 24 mmol) in THF (10 ml) was then added and heating was continued for another 3 hours. The solvent was evaporated, toluene and water were added (50 ml, each) and the phases were separated. A pale yellow oil (7.3 g) was isolated from the organic layer which was treated with light petroleum to yield colourless crystals (5.6 g), melting at 101° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureheating
  4. customThe solvent was evaporated
  5. additiontoluene and water were added (50 ml
  6. customeach) and the phases were separated

Sources & evidence

ORD record
ord-c8ae2a7771a343608595f3b380eb0cbf
Source dataset
uspto-grants-1997_01
Patent number
US05591741

Reaction notes

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