4-Toluenesulfonyl chloride → HCID 87508152, compound

HRID 2196105Notes

Reaction equation

HRID 2196105 reaction equation
[OH:1][CH2:2][C:3]1([CH2:9][OH:10])[CH2:8][CH2:7][S:6][CH2:5][S:4]1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>N1C=CC=CC=1>[C:17]1([CH3:18])[CH:19]=[CH:20][C:14]([S:11]([O:1][CH2:2][C:3]2([CH2:9][O:10][S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH2:8][CH2:7][S:6][CH2:5][S:4]2)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 87508412HCID 87508412, compound

Product 1

HCID 87508152HCID 87508152, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4,4-bis(hydroxymethyl)-[1,3]dithiane (405 mg, 2.25 mmol) and TsCl (1.29 g, 6.75 mmol) in anhydrous pyridine (4 mL) was stirred at rt for 48 h. Solvent was removed in vacuo and co-evaporated with toluene (3×3 mL). CH2Cl2 (40 mL) and sat aq NaHCO3 (40 mL) were added, the phases separated and the organic phase dried (Na2SO4), filtered and concentrated under reduced pressure. The residue obtained was flash chromatographed (35-55% EtOAc in light petroleum) to provide 4,4-bis(p-toluenesulphonyloxymethyl)-[1,3]dithiane (525) as a white solid material.

Workup

  1. customSolvent was removed in vacuo and co-evaporated with toluene (3×3 mL)
  2. additionwere added
  3. customthe phases separated
  4. dry with materialthe organic phase dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customchromatographed (35-55% EtOAc in light petroleum)

Sources & evidence

ORD record
ord-b7d30b8c5c934f40aca38d4e55575939
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

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