p-Toluenesulfonic acid monohydrate → HCID 18625804, compound

HRID 1859951Notes

Reaction equation

HRID 1859951 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:13]([CH2:20][CH2:21][CH:22]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][O:38]C2CCCCO2)=[CH:31][CH:30]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[OH:38][CH2:37][CH2:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][CH:22]([CH2:21][CH2:20][O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18625952HCID 18625952, compound

Product 1

HCID 18625804HCID 18625804, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.40) was added to a solution of ethyl 2-(2-phenoxyethyl)-3-[4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl]propionate (738 mg), which is the product of Reference example 3(e), in ethanol (10 ml). The mixture was stirred at ambient temperature for 2 hours. At the end of this time the reaction mixture was concentrated. The residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate and then concentrated. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=7/3-3/2 as the eluant to afford the desired compound (503 mg) as a syrup.

Workup

  1. concentrationAt the end of this time the reaction mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-933b51d653be46768d304036457e79af
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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