p-Toluenesulfonic acid monohydrate → HCID 11045430, compound

HRID 1596053Notes

Reaction equation

HRID 1596053 reaction equation
O1C([O:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21705620HCID 21705620, compound

Product 1

HCID 11045430HCID 11045430, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 10D (2.0 g, 4.95 mmol) in methanol was treated with para-toluenesulfonic acid hydrate (84 mg, 0.44 mmol), stirred at room temperature for 2 hours, partitioned between ethyl acetate and water, dried (Na2SO4), filtered, concentrated and purified on silica gel with 30% ethyl acetate/hexanes to provide 1.5 g (95%) of the desired compound as an yellow oil.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-291a7fe23baa44b99aae73c8aa445416
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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