HCID 86682912, compound → HCID 86682911, compound

HRID 2368942Notes

Reaction equation

HRID 2368942 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:36]([F:39])([F:38])[F:37])([O:31][Si](C)(C)C)[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:40]C4CCCCO4)[CH:14]=3)[O:9]2)=[CH:4][CH:3]=1>CO.Cl>[OH:24][C:21]1[CH:20]=[CH:19][C:18]([CH:17]2[C:16]([C:36]([F:39])([F:37])[F:38])([OH:31])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:40])[CH:14]=3)[O:9][CH:8]2[C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 86682912HCID 86682912, compound

Product 1

HCID 86682911HCID 86682911, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of {2-(4-iodo-phenyl)-6-(tetrahydro-pyran-2-yloxy)-3-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-4-trifluoromethyl-chroman-4-yloxy}-trimethyl-silane (15 g, 73 mmol) in MeOH (400 mL), concentrated HCl (100 mL) was added. The reaction mixture was stirred at room temperature for 4 h, concentrated, and re-dissolved in DCM (150 mL). The solution was washed (3×100 mL brine), dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (PE/EA=10/1) to afford the desired product (10 g). 1H NMR (DMSO-d6): δ 9.17 (s, 1H), 9.08 (s, 1H), 7.55 (d, 2H), 7.10 (d, 2H), 7.06-6.99 (m, 3H), 6.76-6.65 (m, 2H), 6.55-6.48 (m, 3H), 5.77 (d, 1H), 3.55 (d, 1H); LCMS: 527 (M−H)−.

Workup

  1. concentrationconcentrated
  2. dissolutionre-dissolved in DCM (150 mL)
  3. washThe solution was washed (3×100 mL brine)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (PE/EA=10/1)

Sources & evidence

ORD record
ord-da8a1210017a43faad2df54210080a17
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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