Potassium Carbonate → 2-(2,4-Dichlorophenyl)-5-(oxiran-2-ylmethoxy)benzoxazole

HRID 22726

Reaction equation

HRID 22726 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>[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]([O:18][CH2:19][CH:21]3[CH2:22][O:23]3)=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 149428(+)-EpichlorohydrinHCID 219117282-(2,4-Dichlorophenyl)benzoxazol-5-ol2×

Product 1

HCID 219116592-(2,4-Dichlorophenyl)-5-(oxiran-2-ylmethoxy)benzoxazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-d72bb1d66a474182a6dd290f9bff2a63
Source dataset
uspto-grants-2005_02
Patent number
US06849632B2

Linked notes

Loading…