Thionyl Chloride → (2-Cyclopentyl-5-methyl-1,3-oxazol-4-yl)methanol

HRID 746025Notes

Reaction equation

HRID 746025 reaction equation
[CH:1]1([C:6]2[O:7][C:8]([CH3:14])=[C:9]([C:11](O)=[O:12])[N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O>>[CH:1]1([C:6]2[O:7][C:8]([CH3:14])=[C:9]([CH2:11][OH:12])[N:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 132829272-Cyclopentyl-5-methyl-1,3-oxazole-4-carboxylic acid

Product 1

HCID 23311254(2-Cyclopentyl-5-methyl-1,3-oxazol-4-yl)methanol

Procedure

A mixture of 2-cyclopentyl-5-methyl-4-oxazolecarboxylic acid (7.0 g) and thionyl chloride (14 ml) was refluxed with stirring for 40 minutes. The thionyl chloride was completely distilled off and the residue was dissolved in dimethoxyethane (70 ml). The solution was added dropwise to a mixture of sodium borohydride (2.7 g) and dimethoxyethane (50 ml) with ice-cooling and stirring. The mixture was stirred for 30 minutes, adjusted to pH 2 with 2N hydrochloric acid and refluxed for 30 minutes. The solvent was then distilled off and aqueous sodium hydrogen carbonate was added. The mixture was extracted with ethyl ether and the ethyl ether layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by chromatography using silica gel (75 g) [eluent: hexane-acetone (7:3)] to give 2-cyclopentyl-4-hydoxymethyl-5-methyloxazole as an oil; yield 4.0 g (61.5%).

Workup

  1. temperaturewas refluxed
  2. distillationThe thionyl chloride was completely distilled off
  3. dissolutionthe residue was dissolved in dimethoxyethane (70 ml)
  4. additionThe solution was added dropwise to a mixture of sodium borohydride (2.7 g) and dimethoxyethane (50 ml) with ice-
  5. temperaturecooling
  6. stirringstirring
  7. stirringThe mixture was stirred for 30 minutes
  8. temperaturerefluxed for 30 minutes
  9. distillationThe solvent was then distilled off
  10. additionaqueous sodium hydrogen carbonate was added
  11. extractionThe mixture was extracted with ethyl ether
  12. washthe ethyl ether layer was washed with water
  13. dry with materialdried over anhydrous magnesium sulfate
  14. distillationThe solvent was distilled off
  15. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-9edac8f9f6be43869b99574f1f72443e
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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