p-Toluenesulfonic acid monohydrate → HCID 123773910, compound

HRID 1772408Notes

Reaction equation

HRID 1772408 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH2:21][CH:22]([CH2:29][C:30]1([CH3:36])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[CH:23]2O>C1(C)C=CC=CC=1>[C:13]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH2:21][C:22]([CH2:29][C:30]1([CH3:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1)=[CH:23]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 117817872HCID 117817872, compound

Product 1

HCID 123773910HCID 123773910, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Mixture of p-toluene-sulfonic acid monohydrate (0.38 g, 2.0 mmol, 0.2 equiv), compound 22 (4.0 g crude, ˜9.88 mmol, 1.0 equiv) and toluene (100 mL) was refluxed for 1 hour. After cooling to room temperature, the mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on an AnaLogix (25-80 g) column, eluting with a gradient of 0 to 10% ethyl acetate in heptanes to give compound 23 (2.5 g, 67% yield for 2 steps) as a white solid.

Workup

  1. temperaturewas refluxed for 1 hour
  2. washthe mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on an AnaLogix (25-80 g) column
  7. washeluting with a gradient of 0 to 10% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-259c8bdc21f94bae821f08e9ca01e687
Source dataset
uspto-grants-2016_02
Patent number
US09249239B2

Reaction notes

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