Hydrochloric Acid → HCID 22033299, compound

HRID 1792404Notes

Reaction equation

HRID 1792404 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][S:34][CH2:35][CH2:36][CH2:37][C:38]([F:44])([F:43])[C:39]([F:42])([F:41])[F:40])[CH:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21]COC)=[CH:17][CH:16]=3)[CH2:11][O:12]2)=[CH:7][CH:6]=1.Cl.O>CCO>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][S:34][CH2:35][CH2:36][CH2:37][C:38]([F:44])([F:43])[C:39]([F:40])([F:41])[F:42])[CH:10]([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22033304HCID 22033304, compound

Product 1

HCID 22033299HCID 22033299, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]chroman (204 mg, 0.314 mmol) in EtOH (2 ml) was added 6N HCl (0.2 ml, 1.2 mmol). The resulting solution was stirred between 40 and 45° C. for 17 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, 33% AcOEt/hexane) to afford (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]chroman (140 mg, 80%).

Workup

  1. extractionThe mixture was extracted with AcOEt
  2. washThe organic layer was washed with saturated aqueous NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica gel, 33% AcOEt/hexane)

Sources & evidence

ORD record
ord-e8908afb197149f1a016045aa0013908
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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