Ethyl Propionate → HCID 22437348, compound

HRID 1956129Notes

Reaction equation

HRID 1956129 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1O[C:11](=O)[S:10][N:9]=1.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[C:15]#[CH:16].[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:22]C>CC1C=CC(C)=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:16]=[C:15]([C:14]([O:18][CH2:19][CH3:20])=[O:17])[S:10][N:9]=1.[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:22]([C:21]([O:25][CH2:26][CH3:27])=[O:24])=[CH:11][S:10][N:9]=1

Participants

6

Reactant 3

HCID 7749Ethyl PropionateHCID 12182Ethyl propiolateHCID 12437393HCID 12437393, compound

Product 2

HCID 12437461HCID 12437461, compoundYield 32%HCID 22437348HCID 22437348, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A solution of 5-(2-fluorophenyl)[1,3,4]oxathiazolin-2-one (1.97 g, 10 mmol) and ethyl propiolate (1.96 g, 20 mmol) in p-xylene is heated at reflux temperature for 48 h, treated with a further portion of ethyl propionate, heated at reflux temperature for another 48 h, and distilled to remove the solvent. The resultant residue is purified by flash column chromatography (silica gel, toluene) to give ethyl 3-(2-fluorophenyl)isothiazole-5-carboxylate (1.0 g, 40%) as yellow crystals, mp 53°-54° C., plus ethyl 3-(2-fluorophenyl)isothiazole-4-carboxylate (0.8 g, 32%) as a yellow oil.

Workup

  1. temperatureat reflux temperature for 48 h
  2. temperatureheated
  3. temperatureat reflux temperature for another 48 h
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe resultant residue is purified by flash column chromatography (silica gel, toluene)

Sources & evidence

ORD record
ord-139f916791d0425cbb3b0ecfd9e8a8cb
Source dataset
uspto-grants-1998_07
Patent number
US05780393

Reaction notes

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