Thionyl Chloride → {2-[2-(2-Chlorophenyl)ethenyl]-5-methyl-1,3-oxazol-4-yl}methanol

HRID 746019Notes

Reaction equation

HRID 746019 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH:4]=[CH:5][C:6]1[O:7][C:8]([CH3:14])=[C:9]([C:11](O)=[O:12])[N:10]=1.S(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH:4]=[CH:5][C:6]1[O:7][C:8]([CH3:14])=[C:9]([CH2:11][OH:12])[N:10]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 542352702-[2-(2-Chlorophenyl)ethenyl]-5-methyl-1,3-oxazole-4-carboxylic acid

Product 1

HCID 54261692{2-[2-(2-Chlorophenyl)ethenyl]-5-methyl-1,3-oxazol-4-yl}methanol

Procedure

A mixture of 2-(2-chlorostyryl)-5-methyl-4-oxazolecarboxylic acid (4.8 g) and thionyl chloride (24 ml) was refluxed with stirring for an hour. The thionyl chloride was distilled off and the crystalline residue (acid chloride) was washed with isopropyl ether and dissolved in dimethoxyethane (20 ml). The solution was added dropwise to a suspension of sodium borohydride (1.4 g) in dimethoxyethane (30 ml) with ice-cooling and stirring. The reaction was allowed to proceed under ice-cooling for 30 minutes and the reaction mixture was adjusted to pH 2 with 2N hydrochloric acid and refluxed for 30 minutes. The solvent was then distilled off and the residue was neutralized with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the resulting crystalline precipitate was collected by filtration and washed with isopropyl ether to give 2-(2-chlorostyryl)-4-hydroxymethyl-5-methyloxazole; yield 3.9 g (85.9%). Recrystallization from ethanol gave colorless needles melting at 122°-123° C.

Workup

  1. temperaturewas refluxed
  2. distillationThe thionyl chloride was distilled off
  3. washthe crystalline residue (acid chloride) was washed with isopropyl ether
  4. dissolutiondissolved in dimethoxyethane (20 ml)
  5. additionThe solution was added dropwise to a suspension of sodium borohydride (1.4 g) in dimethoxyethane (30 ml) with ice-
  6. temperaturecooling
  7. stirringstirring
  8. temperaturecooling for 30 minutes
  9. temperaturerefluxed for 30 minutes
  10. distillationThe solvent was then distilled off
  11. extractionextracted with ethyl acetate
  12. washThe ethyl acetate layer was washed with water
  13. dry with materialdried over anhydrous magnesium sulfate
  14. distillationThe solvent was distilled off
  15. filtrationthe resulting crystalline precipitate was collected by filtration
  16. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-15a7cb53b0934c5b809baf22a77ad2ec
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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