Epichlorohydrin → HCID 86643049, compound

HRID 2065916Notes

Reaction equation

HRID 2065916 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[C:18]([CH2:24][CH3:25])[CH:17]=3)[N:12]=2)[CH:6]=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2].[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>C(O)(C)C.[OH-].[Na+].CC(=O)OCC>[CH2:9]([C:8]1[C:3]([CH2:1][CH3:2])=[CH:4][C:5]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[C:20]([CH3:22])[C:19]([O:23][CH2:26][CH:28]4[CH2:29][O:30]4)=[C:18]([CH2:24][CH3:25])[CH:17]=3)[N:12]=2)=[CH:6][N:7]=1)[CH3:10]

Participants

6

Reactant 2

HCID 7835EpichlorohydrinHCID 136170273HCID 136170273, compound

Product 1

HCID 86643049HCID 86643049, compoundYield 52.5%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol (150 mg, 0.445 mmol) in isopropanol (10 mL) and 3 N aq. NaOH (3 mL), epichlorhydrine (164 mg, 1.78 mmol) is added. The mixture is stirred at rt for 20 h. The mixture is diluted with EA and washed with sat. aq. NaHCO3 solution. The org. extract is dried over MgSO4, filtered and evaporated. The crude product is purified by chromatography on prep. TLC plates with EA-heptane to give (RS)-2,3-diethyl-5-[3-(3-ethyl-5-methyl-4-oxiranylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-pyridine (92 mg) as an oil.

Workup

  1. washwashed with sat. aq. NaHCO3 solution
  2. extractionextract
  3. dry with materialis dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by chromatography on prep

Sources & evidence

ORD record
ord-4aab7bacf12c4bb9a063d4bab2305adb
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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