p-Toluenesulfonic acid monohydrate → HCID 23111796, compound

HRID 273373Notes

Reaction equation

HRID 273373 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23]C3CCCCO3)[CH:17]=2)=[C:11]([CH3:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[CH:17]=2)=[C:11]([CH3:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58903108HCID 58903108, compound

Product 1

HCID 23111796HCID 23111796, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-{[4′-(benzyloxy)-2′,6′-dimethylbiphenyl-3-yl]methoxy}tetrahydro-2H-pyran (1.71 g, 4.25 mmol) and p-toluenesulfonic acid monohydrate (80.8 mg, 0.425 mmol) in methanol (15 mL) was stirred at room temperature for 20 hrs. The reaction solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-50% ethyl acetate/hexane) to give the title compound (1.13 g, yield 84%) as a colorless oil.

Workup

  1. customThe reaction solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (20%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d157916b3b434208be475c80998b0890
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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