p-Toluenesulfonic acid monohydrate → HCID 123710782, compound

HRID 1772405Notes

Reaction equation

HRID 1772405 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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]([CH3:29])[CH:23]2O>C1(C)C=CC=CC=1>[C:13]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=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]([CH3:29])=[CH:23]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 117817968HCID 117817968, compound

Product 1

HCID 123710782HCID 123710782, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of p-toluenesulfonic acid monohydrate (1.57 g, 8.26 mmol, 0.2 equiv), compound 18 (13.0 g crude, 41.17 mmol, 1.0 equiv) and toluene (300 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 (65-200 g) column, eluting with a gradient of 0 to 10% ethyl acetate in heptanes to give compound 19 (10.25 g, 88% overall 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 (65-200 g) column
  7. washeluting with a gradient of 0 to 10% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-8a3b9b90022545498304bb9ce3b64acc
Source dataset
uspto-grants-2016_02
Patent number
US09249239B2

Reaction notes

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