p-Toluenesulfonic acid → 2-Phenyl-4-(pyrid-3-yl)-5-(2-bromophenyl)-1,3-dioxolane

HRID 1613647Notes

Reaction equation

HRID 1613647 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:17])(O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Br:15])[CH:2]=1.C[O:19][CH:20](OC)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1.C1(C)C=CC=CC=1>[C:21]1([CH:20]2[O:17][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[Br:15])[O:19]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 62375Benzaldehyde dimethyl acetalHCID 197741971-(Pyrid-3-yl)-2-(2-bromophenyl)-ethanediol

Product 1

HCID 197742082-Phenyl-4-(pyrid-3-yl)-5-(2-bromophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 18994452Chlorobenzene tolueneSolvent

Procedure

37 g (0.1258 mol) of 1-(pyrid-3-yl)-2-(2-bromophenyl)-ethanediol and 38.5 g (0.2516 mol) of benzaldehyde dimethyl acetal were refluxed together in 440 ml of 10:1 chlorobenzene/toluene with 1 g of p-toluenesulfonic acid. The resulting methanol was distilled off as an azeotrope with toluene. After the end of the reaction, the chlorobenzene was distilled off under reduced pressure and the product wa purified by chromatography over silica gel.

Workup

  1. distillationThe resulting methanol was distilled off as an azeotrope with toluene
  2. customAfter the end of the reaction
  3. distillationthe chlorobenzene was distilled off under reduced pressure
  4. customthe product wa purified by chromatography over silica gel

Sources & evidence

ORD record
ord-44799372e3b448cca7597c756cfd0536
Source dataset
uspto-grants-1993_03
Patent number
US05194441

Reaction notes

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