Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate → S-Tetrahydro-2H-pyran-4-YL ethanethioate

HRID 1924864Notes

Reaction equation

HRID 1924864 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[O:6]1[CH2:11][CH2:10][CH:9](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:8][CH2:7]1>CN(C=O)C.CCOCC>[O:6]1[CH2:11][CH2:10][CH:9]([S:3][C:1](=[O:4])[CH3:2])[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonateHCID 23670855Potassium ethanethioate

Product 1

HCID 18533108S-Tetrahydro-2H-pyran-4-YL ethanethioate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of potassium thioacetate (10.21 g; 87.62 mmol) and toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester (11.23 g; 43.81 mmol) in DMF (100 mL) was heated at 50° C. for 12 hours, cooled to room temperature, diluted with ether, washed with water, saturated NaHCO3 and brine and dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was taken forward without additional purification.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water, saturated NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. customRemoval of the volatiles in vacuo
  5. customprovided a residue which
  6. customwas taken forward without additional purification

Sources & evidence

ORD record
ord-76cde16224864ccb931e60eada60c49d
Source dataset
uspto-grants-2012_05
Patent number
US08178568B2

Reaction notes

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