Hydrochloric Acid → HCID 23147391, compound

HRID 495297Notes

Reaction equation

HRID 495297 reaction equation
[CH2:1]([C:3]1[C:8]([O:9]COC)=[CH:7][C:6]([O:13]COC)=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:4]=1[CH2:23][CH2:24][C:25]1[O:29][CH:28]=[N:27][C:26]=1[CH2:30][OH:31])[CH3:2].O1CCOCC1.Cl.[OH-].[Na+]>CO>[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([OH:13])=[C:5]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:4]=1[CH2:23][CH2:24][C:25]1[O:29][CH:28]=[N:27][C:26]=1[CH2:30][OH:31])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 23147113HCID 23147113, compound

Product 1

HCID 23147391HCID 23147391, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5-{2-[2-Ethyl-3,5-bis(methoxymethoxy)-6-phenylphenyl]ethyl}-1,3-oxazol-4-yl)methanol (200 mg) was dissolved in methanol (5.0 mL), and 1,4-dioxane solution (1 ml) of 4.0 mol/L hydrochloric acid was added thereto and stirred at room temperature for 3 hours. The reaction liquid was neutralized with aqueous sodium hydroxide solution (1 mol/L), and then extracted with chloroform. The organic layer was washed with aqueous saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through preparative thin-layer column chromatography (chloroform/methanol=9/1) to obtain Compound 210 (53 mg, 39%).

Workup

  1. customThe reaction liquid
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. customThe resulting residue was purified through preparative thin-layer column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-f7193738254b47dab99e036e0fb51ca9
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

Loading…