Water → HCID 22033229, compound

HRID 1792405Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH2:29][CH2:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])[CH:7]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[CH2:8][O:9]2)=[CH:4][CH:3]=1.O.[OH:40]OS([O-])=O.[K+]>C1COCC1>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28]([CH2:29][CH2:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:34])([F:35])[F:36])=[O:40])[CH:7]([C:12]3[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=3)[CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]chroman (140 mg, 0.250 mmol) and H2O (0.05 ml) in THF (1.2 ml) at 0° C. was added Oxone® (monopersulfate compound; DuPont product) (77 mg, 0.125 mmol). The resulting solution was stirred at 0° C. for 3.5 hr, and then poured into H2O. The mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4, filtered, concentrated, and purified by column chromatography (silica gel, 60% AcOEt/hexane) to afford (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-4-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]chroman (105 mg, 73%).

Workup

extractionThe mixture was extracted with AcOEt
washThe organic layer was washed with saturated aqueous NaCl
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by column chromatography (silica gel, 60% AcOEt/hexane)

Sources & evidence

ORD record: ord-f9fd6cf2533f4847b46d5d3daee6cddd
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074819B2

Reaction notes

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