Epichlorohydrin → HCID 86640706, compound

HRID 1666591Notes

Reaction equation

HRID 1666591 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[C:18]([CH3:24])[CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl>C(O)(C)C.[OH-].[Na+].CC(=O)OCC>[CH3:22][C:20]1[CH:21]=[C:16]([C:13]2[N:12]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=3)[O:15][N:14]=2)[CH:17]=[C:18]([CH3:24])[C:19]=1[O:23][CH2:25][CH:27]1[CH2:28][O:29]1

Participants

6

Reactant 2

HCID 7835EpichlorohydrinHCID 136085236HCID 136085236, compound

Product 1

HCID 86640706HCID 86640706, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-[5-(4-isopropoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol (370 mg, 1.14 mmol) and epichlorohydrine (317 mg, 3.42 mmol) in isopropanol (5 mL) and 3 N aq. NaOH (1.5 mL) is stirred at rt for 16 h. The mixture is diluted with EA, washed with water, dried over MgSO4, filtered and concentrated. The crude product is purified by chromatography on prep. TLC plates with heptane:EA 3:1 to give 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-5-(4-isopropoxy-phenyl)-[1,2,4]oxadiazole (256 mg) as white solid; LC-MS: tR=1.14 min, [M+1]+=381.18.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by chromatography on prep

Sources & evidence

ORD record
ord-6caa92716dba469db5e9946cd272dcf4
Source dataset
uspto-grants-2011_10
Patent number
US08044076B2

Reaction notes

Loading…