p-Toluenesulfonic acid monohydrate → HCID 58755286, compound

HRID 1163319Notes

Reaction equation

HRID 1163319 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C2CCCCO2)[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]3[CH:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH2:28][O:29][C:25]=3[CH:24]=2)[CH:16]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:8][C:6]1[CH:5]=[CH:4][C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:23]3[CH:36]=[CH:35][C:26]4[CH:27]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH2:28][O:29][C:25]=4[CH:24]=3)[CH:16]=2)=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58755281HCID 58755281, compound

Product 1

HCID 58755286HCID 58755286, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (6-{[2′-methyl-4′-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-yl]methoxy}-2,3-dihydro-1-benzofuran-3-yl)acetate (4.49 g, 9.19 mmol) and p-toluenesulfonic acid monohydrate (0.175 g, 0.919 mmol) in methanol (50 mL) was stirred at room temperature for 30 hr. 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%-60% ethyl acetate/hexane) to give the title compound (3.21 g, yield 86%) as a colorless viscous 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%-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8e0b01320f214faea1707e6fdfdd2910
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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