Thionyl Chloride → 5-(Chloromethyl)-3-methoxy-1,2-oxazole

HRID 2351305Notes

Reaction equation

HRID 2351305 reaction equation
O[CH2:2][C:3]1[O:7][N:6]=[C:5]([O:8][CH3:9])[CH:4]=1.S(Cl)([Cl:12])=O>>[Cl:12][CH2:2][C:3]1[O:7][N:6]=[C:5]([O:8][CH3:9])[CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 106782583-Methoxy-5-isoxazolemethanol

Product 1

HCID 100805435-(Chloromethyl)-3-methoxy-1,2-oxazoleYield 70%

Procedure

The mixture of 12.05 g of 5-hydroxymethyl-3-methoxy-isoxazole and 43 g of thionylchloride is heated to reflux for 30 minutes. After cooling, the reaction mixture is poured slowly over crushed ice and is extracted with ether. The organic phase is separated, washed with water and the solution is dried over magnesium sulfate. The solvent is evaporated then distilled in vacuo. 9.64 g of the expected product are obtained.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 30 minutes
  3. temperatureAfter cooling
  4. additionthe reaction mixture is poured slowly
  5. customover crushed ice
  6. extractionis extracted with ether
  7. customThe organic phase is separated
  8. washwashed with water
  9. dry with materialthe solution is dried over magnesium sulfate
  10. customThe solvent is evaporated
  11. distillationthen distilled in vacuo

Sources & evidence

ORD record
ord-7d2ea957315e4ca6b0cc6ce92603213c
Source dataset
uspto-grants-1989_10
Patent number
US04873243

Reaction notes

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