4-Toluenesulfonyl chloride → 1,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)

HRID 1509860Notes

Reaction equation

HRID 1509860 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C1N2CCN(CC2)C1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][S:26]([C:23]3[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=3)(=[O:28])=[O:27])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

Product 1

HCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)Yield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,4-dioxa-spiro[4.5]decan-8-ol (1.0 mg, 6.3 mmol) and triethylenediamine (0.780 mg, 7.0 mmol) cooled to 0° C. in DCM (20 mL) was added p-toluenesulfonylchloride (1.31 g, 7.0 mmol) in DCM (5 mL). The reaction mixture was stirred overnight and then washed with 0.5 N HCl (20 mL). The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound (2.0 g) which was used without further purification.

Workup

  1. washwashed with 0.5 N HCl (20 mL)
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-288a2a89668e4f23aca84dd500066afb
Source dataset
uspto-grants-2012_07
Patent number
US08211894B2

Reaction notes

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