p-Toluenesulfonic acid monohydrate → HCID 57413460, compound

HRID 273399Notes

Reaction equation

HRID 273399 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C2CCCCO2)[CH:5]=[C:4]([CH3:15])[C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:26][CH:25]=2)[CH:17]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]3[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:28][CH:29]=3)[CH:17]=2)=[C:4]([CH3:15])[CH:5]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58903114HCID 58903114, compound

Product 1

HCID 57413460HCID 57413460, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-[4-[[2′,6′-dimethyl-4′-(tetrahydro-2H-pyran-2-yloxy)biphenyl-3-yl]methoxy]phenyl]propanoate (2.92 g, 6.15 mmol), p-toluenesulfonic acid monohydrate (0.12 g, 0.62 mmol) and methanol (60 mL) was stirred at room temperature for 2 hrs., and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/2) to give the title compound (2.12 g, yield 88%) as a red oil.

Workup

  1. concentration, and the mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-f5a5bcd2da6643508b65e839cca70e08
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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