4-Toluenesulfonyl chloride → Toluene-4-sulfonic Acid 2-[4-(2-Hydroxyethyl)-phenyl]ethyl Ester

HRID 225794Notes

Reaction equation

HRID 225794 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.C1N2CCN(CC2)C1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C1COCC1>[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][S:27]([C:24]2[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=2)(=[O:29])=[O:28])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 50132051,4-Benzenediethanol

Product 1

HCID 87668833Toluene-4-sulfonic Acid 2-[4-(2-Hydroxyethyl)-phenyl]ethyl EsterYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the intermediate from Step A in THF (50 mL) was added DABCO (1.51 g, 13.5 mmol) and then p-toluenesulfonyl chloride (50 mL). The resulting mixture was stirred overnight at room temperature and then filtered to remove precipitated hydrochloride salts. The filtrate was concentrated under reduced pressure and DCM (50 mL) was added to the residue. The organic layer was then washed with water (1×100 mL), saturated NaCl (1×100 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The resulting material was purified by silica gel chromatography (70% EtOAc/hexane) to afford 1.25 g of the title intermediate (43% yield).

Workup

  1. filtrationfiltered
  2. customto remove
  3. customprecipitated hydrochloride salts
  4. concentrationThe filtrate was concentrated under reduced pressure and DCM (50 mL)
  5. additionwas added to the residue
  6. washThe organic layer was then washed with water (1×100 mL), saturated NaCl (1×100 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customThe resulting material was purified by silica gel chromatography (70% EtOAc/hexane)

Sources & evidence

ORD record
ord-7bf22b05f1f44d99bf82834facdb0bfa
Source dataset
uspto-grants-2009_07
Patent number
US07557126B2

Reaction notes

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