HCID 11157748, compound → HCID 11433555, compound

HRID 2374646Notes

Reaction equation

HRID 2374646 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][S:32][CH2:33][CH2:34][CH2:35][C:36]([F:42])([F:41])[C:37]([F:40])([F:39])[F:38])=[CH:23][CH:22]=3)=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]3)=[CH:5][CH:4]=1.I([O-])(=O)(=O)=[O:44].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10]([O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][S:32]([CH2:33][CH2:34][CH2:35][C:36]([F:41])([F:42])[C:37]([F:40])([F:39])[F:38])=[O:44])=[CH:23][CH:22]=3)=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]3)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 11157748HCID 11157748, compoundHCID 23667635Sodium periodate

Product 1

HCID 11433555HCID 11433555, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve 6-(4-methoxy-phenyl)-5-{4-[4-(4,4,5,5,5-pentafluoro-pentylsulfanyl)-butoxy]-phenoxy}-naphthalen-2-ol (0.313 g, 0.516 mmol) in MeOH (15 mL). Add sodium periodate (0.122 g, 0.570 mmol) in H2O (2 mL). Stir overnight at room temperature. Extract with EtOAc (30 mL). Wash with H2O (15 mL), NaHCO3 (saturated solution, 15 mL), brine (20 mL). Dry the organics (Na2SO4), filter and concentrate in vacuo. Purify by radial chromatography (eluting with 50% EtOAc, 48% Hexanes, 2% MeOH) to afford 0.185 mg (58%) of the desired 6-(4-Methoxy-phenyl)-5-{4-[4-(4,4,5,5,5-pentafluoro-pentane-sulfinyl)-butoxy]-phenoxy}-naphthalen-2-ol as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.79 (d, J=8.8 Hz, 1H), 7.55 (d, J=8.3 Hz, 1H), 7.47 (m, 3H), 7.19 (m, 1H), 7.02 (m, 1H), 6.82 (d, J=8:8 Hz, 2H), 6.57 (s, 4H), 3.76 (m, 5H), 2.65-2.84 (m, 4H), 2.10-2.25 (m, 4H), 1.79-1.93 (m, 4H). MS (ion spray): ES+: 623 (M+1); ES−: 621 (M−1).

Workup

  1. extractionExtract with EtOAc (30 mL)
  2. washWash with H2O (15 mL), NaHCO3 (saturated solution, 15 mL), brine (20 mL)
  3. dry with materialDry the organics (Na2SO4)
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify by radial chromatography (eluting with 50% EtOAc, 48% Hexanes, 2% MeOH)

Sources & evidence

ORD record
ord-27a02fe939f9404eb36542096077c435
Source dataset
uspto-grants-2008_12
Patent number
US07462647B2

Reaction notes

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