Potassium Carbonate → 5-[((2R)oxiran-2-yl)methoxy]-2-(2,4-dichlorophenyl)benzoxazole

HRID 1245366Notes

Reaction equation

HRID 1245366 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:12]=2[N:13]=1.[CH2:19]([C@H:21]1[O:23][CH2:22]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:23]1[CH2:22][C@@H:21]1[CH2:19][O:18][C:15]1[CH:16]=[CH:17][C:11]2[O:10][C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[N:13][C:12]=2[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 149428(+)-EpichlorohydrinHCID 219117282-(2,4-Dichlorophenyl)benzoxazol-5-ol

Product 1

HCID 587196605-[((2R)oxiran-2-yl)methoxy]-2-(2,4-dichlorophenyl)benzoxazoleYield 77.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(2,4-dichlorophenyl)benzoxazol-5-ol (6.0 g, 36 mmol), (S)-(+)-epichlorohydrin (3.3 g, 315 mmol) (20 ml, 182 mmol), and potassium carbonate (20 g, 144 mmol) in acetone (100 ml) was heated to reflux and allowed to stir overnight. The solution was allowed to cool and filtered through Celite 512. The filtrate was evaporated under reduced pressure to yield an oil, which was chromatographed on silica gel, eluting with 20% ethyl acetate/hexanes, to yield 5-[((2R)oxiran-2-yl)methoxy]-2-(2,4-dichlorophenyl)benzoxazole as white solid (6.2 g, 28 mmol).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureto cool
  4. filtrationfiltered through Celite 512
  5. customThe filtrate was evaporated under reduced pressure
  6. customto yield an oil, which
  7. customwas chromatographed on silica gel
  8. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b491b45b40b0465aa5a2a0879c748e14
Source dataset
uspto-grants-2006_10
Patent number
US07125876B2

Reaction notes

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