Thionyl Chloride → [5-Ethyl-2-(2-phenylethenyl)-1,3-oxazol-4-yl]methanol

HRID 746024Notes

Reaction equation

HRID 746024 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:5][C:4]=1[C:16](O)=[O:17])[CH3:2].S(Cl)(Cl)=O>>[CH2:1]([C:3]1[O:7][C:6]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:5][C:4]=1[CH2:16][OH:17])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 542006445-Ethyl-2-(2-phenylethenyl)-1,3-oxazole-4-carboxylic acid

Product 1

HCID 53750562[5-Ethyl-2-(2-phenylethenyl)-1,3-oxazol-4-yl]methanol

Procedure

A mixture of 5-ethyl-2-styryl-4-oxazolecarboxylic acid (5.57 g) and thionyl chloride (17 ml) was refluxed with stirring for an hour and the thionyl chloride was completely distilled off. The residue was dissolved in dimethoxyethane (20 ml) and the solution was added dropwise to a mixture of sodium borohydride (1.74 g) and dimethoxyethane (50 ml) under cooling with ice-sodium chloride and stirring. The whole mixture was stirred for 15 minutes, adjusted to pH 2 with 2N hydrochloric acid and refluxed for 30 minutes. The reaction mixture was concentrated, 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 then distilled off and the residue was treated with hexane to give 5-ethyl-4-hydroxymethyl-2-styryloxazole as crystals; yield 4.37 g (83.4%). Recrystallization from ethyl ether gave colorless prisms melting at 90°-91° C.

Workup

  1. temperaturewas refluxed
  2. distillationthe thionyl chloride was completely distilled off
  3. dissolutionThe residue was dissolved in dimethoxyethane (20 ml)
  4. additionthe solution was added dropwise to a mixture of sodium borohydride (1.74 g) and dimethoxyethane (50 ml)
  5. temperatureunder cooling with ice-sodium chloride
  6. stirringstirring
  7. stirringThe whole mixture was stirred for 15 minutes
  8. temperaturerefluxed for 30 minutes
  9. concentrationThe reaction mixture was concentrated
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. distillationThe solvent was then distilled off
  14. additionthe residue was treated with hexane

Sources & evidence

ORD record
ord-b42a7614b71547b7a85d927139a6a7b2
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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