Ethanol → HCID 21290723, compound

HRID 623226Notes

Reaction equation

HRID 623226 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:14][O:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:26](O)[CH3:27]>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:14][O:15][C:16]([CH3:21])([CH3:20])[C:17]([O:19][CH2:26][CH3:27])=[O:18])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 71321Romazarit

Product 1

HCID 21290723HCID 21290723, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

4.44 g (14.5 mmol) of 2-[[2-(4-chlorophenyl)-4-methyl-5-oxazolyl]methoxy]-2-methylpropionic acid were dissolved in 40 ml of dry dichloromethane and 1 drop of dimethylformamide was added. 1.9 g (16 mmol) of thionyl chloride were added and the mixture was heated to reflux for 4 hours. 70 ml of ethanol were added slowly to a stirred solution of the thus-obtained acid chloride at 0° C. and the mixture was stirred for 18 hours. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel using 17% by volume ethyl acetate in hexane for the elution. After evaporation of the eluate there were obtained 2.8 g (57.2%) of ethyl 2-[[2-(4-chlorophenyl)-4-methyl-5-oxazolyl]methoxy]-2-methylpropionate of melting point 75°-76° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by chromatography on silica gel using 17% by volume ethyl acetate in hexane for the elution
  5. customAfter evaporation of the eluate there

Sources & evidence

ORD record
ord-cc9e99f71f284c238bdd58e4369603f6
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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