Water → HCID 22033199, compound

HRID 1792328Notes

Reaction equation

HRID 1792328 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:39])[CH:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:27][CH2:28][CH2:29][CH2:30][C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33])[C:16]3[C:11](=[CH:12][C:13]([OH:38])=[CH:14][CH:15]=3)[S:10][CH2:9]2)=[CH:4][CH:3]=1.[OH:40]OS([O-])=O.[K+].O.CCCCCC>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:39])[CH:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:27]([CH2:28][CH2:29][CH2:30][C:31]([F:37])([F:36])[C:32]([F:33])([F:34])[F:35])=[O:40])[C:16]3[C:11](=[CH:12][C:13]([OH:38])=[CH:14][CH:15]=3)[S:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 8058HexaneHCID 22033449HCID 22033449, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22033199HCID 22033199, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3RS,4RS)-3-(4-fluorophenyl)-7-hydroxy-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]thiochroman (107 mg, 0.18 mmol) in tetrahydrofuran (8 ml) was added Oxone® (monopersulfate compound; DuPont product) (60 mg, 0.1 0 mmol), which was then stirred at 0° C. for 5 minutes. Water (0.5 ml) was added thereto, and the resulting mixture was stirred at 0° C. for 1 hour. The reaction solution was poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product. The crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=2:1) to give (3RS,4RS)-3-(4-fluorophenyl)-7-hydroxy-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]thiochroman (73 mg, yield 66%).

Workup

  1. stirringthe resulting mixture was stirred at 0° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a crude product
  6. customThe crude product thus obtained

Sources & evidence

ORD record
ord-a24f98acb4ce4a499920800099682a3f
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

Loading…