Methyl propionate → 3-(4-Benzyloxy-phenyl)-isothiazol-5-carboxylic acid methyl ester

HRID 72316Notes

Reaction equation

HRID 72316 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2OC(=O)[S:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][CH3:26])(=[O:24])[CH2:22][CH3:23]>ClC1C=CC=CC=1>[CH3:26][O:25][C:21]([C:22]1[S:17][N:16]=[C:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:14][CH:13]=2)[CH:23]=1)=[O:24]

Participants

4

Reactant 2

HCID 11124Methyl propionateHCID 595495255-(4-Benzyloxyphenyl)-[1,3,4]oxathiazol-2-one

Product 1

HCID 666177513-(4-Benzyloxy-phenyl)-isothiazol-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

5-(4-benzyloxy-phenyl)-[1,3,4]oxathiazol-2-one (0.4 g, 1.4 mmol) and 0.23 ml of methyl propionate were dissolved in 10 ml of chlorobenzene and then refluxed overnight. The solvent was distilled off under reduced pressure and the obtained crude compound was purified by silica gel column chromatography to obtain 3-(4-benzyloxy-phenyl)-isothiazol-5-carboxylic acid methyl ester as a desired compound.

Workup

  1. temperaturerefluxed overnight
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe obtained crude compound
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bae299a0dd6140dd87b26a0cdc892800
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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