p-Toluenesulfonic acid → HCID 86682913, compound

HRID 2368943Notes

Reaction equation

HRID 2368943 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:17]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C4CCCCO4)=[CH:20][CH:19]=3)[C:16]([C:32]([F:35])([F:34])[F:33])(O)[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:36]C4CCCCO4)[CH:14]=3)[O:9]2)=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]2[CH:8]([C:5]3[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=3)[O:9][C:10]3[C:15]([C:16]=2[C:32]([F:35])([F:33])[F:34])=[CH:14][C:13]([OH:36])=[CH:12][CH:11]=3)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86682914HCID 86682914, compound

Product 1

HCID 86682913HCID 86682913, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-iodo-phenyl)-6-(tetrahydro-pyran-2-yloxy)-3-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-4-trifluoromethyl-chroman-4-ol (3.0 g, 5.7 mmol) and TsOH (0.6 g, 3.18 mmol) in toluene (60 mL) was refluxed for 18 h, removing water with a Dean Stark trap. The mixture was cooled to room temperature and concentrated. The residue was purified by silica gel column chromatography (PE/EA=10/˜14/1) to afford a white solid (1.5 g). 1H NMR (DMSO-d6): δ 9.17 (s, 1H), 9.07 (s, 1H), 7.56-7.54 (m, 2H), 7.35-6.95 (m, 5H), 6.67-6.50 (m, 4H), 5.73 (s, 1H). LCMS: 509 (M−H)−.

Workup

  1. temperaturewas refluxed for 18 h
  2. customremoving water with a Dean Stark trap
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (PE/EA=10/˜14/1)

Sources & evidence

ORD record
ord-09d19adbeb2d4434931e8ba83c1f6081
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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