Sulfuric Acid → 2-Phenyl-4-(pyrid-3-yl)-4-ethenyl-5-(2-chlorophenyl)-1,3-dioxolane

HRID 1613649Notes

Reaction equation

HRID 1613649 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:19])([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[OH:11])[CH:8]=[CH2:9])[CH:2]=1.OS(O)(=O)=O>COC(OC)C1C=CC=CC=1>[C:12]1([CH:10]2[O:19][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)([CH:8]=[CH2:9])[CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[O:11]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 197741953-(Pyrid-3-yl)-4-(2-chlorophenyl)but-1-ene-3,4-diol

Product 1

HCID 197742132-Phenyl-4-(pyrid-3-yl)-4-ethenyl-5-(2-chlorophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 62375Benzaldehyde dimethyl acetalSolvent

Procedure

3 g (0.018 mol) of 3-(pyrid-3-yl)-4-(2-chlorophenyl)but-1-ene-3,4-diol were dissolved in 50 ml of benzaldehyde dimethyl acetal. 1 ml of concentrated H2SO4 was then added and the mixture was heated to 80°-90° C. The excess benzaldehyde dimethyl acetal was distilled off under reduced pressure, together with the resulting methanol. The crude product was dissolved in methylene chloride and the solution was neutralized with NaHCO3 solution. After the solvent had been separated off, the product was purified by chromatography.

Workup

  1. temperaturethe mixture was heated to 80°-90° C
  2. distillationThe excess benzaldehyde dimethyl acetal was distilled off under reduced pressure, together with the resulting methanol
  3. dissolutionThe crude product was dissolved in methylene chloride
  4. customAfter the solvent had been separated off
  5. customthe product was purified by chromatography

Sources & evidence

ORD record
ord-0d6948a14139470393138fbdb2da9061
Source dataset
uspto-grants-1993_03
Patent number
US05194441

Reaction notes

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