HCID 18363315, compound → HCID 178439107, compound

HRID 1601356Notes

Reaction equation

HRID 1601356 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][S:7][CH:8]([CH2:11][OH:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.[F:15][C:16]([F:29])([F:28])[C:17]1[CH:27]=[CH:26][C:20](/[CH:21]=[C:22](\[CH3:25])/[CH:23]=O)=[CH:19][CH:18]=1>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][S:7][C@@H:8]2[CH2:11][O:12][C@@H:23](/[C:22](/[CH3:25])=[CH:21]/[C:20]3[CH:26]=[CH:27][C:17]([C:16]([F:15])([F:28])[F:29])=[CH:18][CH:19]=3)[O:10][CH2:9]2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 18363315HCID 18363315, compoundHCID 86754756HCID 86754756, compound

Product 1

HCID 178439107HCID 178439107, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

In 12 ml of benzene were dissolved 341 mg (1.46 mmol) of 2-[(4-chlorobenzyl)thio]-1,3-propanediol and 375 mg (1.75 mmol) of (E)-4-(trifluoromethyl)-α-methylcinnamaldehyde, and 3 mg of p-toluenesulfonic acid were added to the solution, followed by heating of the resulting mixture with reflux under nitrogen atmosphere for 2 hours. After cooling, the reaction mixture was washed with an aqueous sodium hydrogencarbonate solution. The residue obtained by evaporation of the solvent was subjected to column chromatography using 15 g of silica gel. The fractions eluted with a mixed solvent of hexane-ethyl acetate (9:1) were collected and the thus obtained solid was washed with hexane to obtain 370 mg (yield: 59%) of the title compound having a melting point of 93 to 95° C.

Workup

  1. additionwere added to the solution
  2. temperatureby heating of the resulting mixture
  3. temperaturewith reflux under nitrogen atmosphere for 2 hours
  4. temperatureAfter cooling
  5. washthe reaction mixture was washed with an aqueous sodium hydrogencarbonate solution
  6. customThe residue obtained by evaporation of the solvent
  7. washThe fractions eluted with a mixed solvent of hexane-ethyl acetate (9:1)
  8. customwere collected
  9. washthe thus obtained solid was washed with hexane

Sources & evidence

ORD record
ord-c2375b85ad89494e8cf2a14e4250ae74
Source dataset
uspto-grants-1999_11
Patent number
US05977152

Reaction notes

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