Water → HCID 19982191, compound

HRID 1460549Notes

Reaction equation

HRID 1460549 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7]2([CH2:12]Br)[O:11][CH2:10][CH2:9][O:8]2)=[CH:3][CH:2]=1.[OH:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7]2([CH2:12][O:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[O:11][CH2:10][CH2:9][O:8]2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 13170394HCID 13170394, compound

Product 1

HCID 19982191HCID 19982191, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2-([1,1'-bipheny]-4-yl)-2-(bromomethyl)-1,3-dioxolane (16 g.), 3-hydroxypyridine (5.7 g.) and potassium carbonate (9 g.) were refluxed with stirring in N,N-dimethylacetamide (75 ml.) for 18 hours. After refluxing, the mixture was allowed to cool and was thereafter poured into water (150 ml.). The resultant aqueous solution was extracted twice with ether. The combined ether fractions were washed once with 5% aqueous sodium hydroxide and 4 times with water. The washed ether fractions were then dried, filtered and the solvent evaporated to yield 3-[[2-([1,1'-biphenyl]-4-yl)-1,3-dioxolan-2-yl]methoxy]pyridine as an oil.

Workup

  1. temperaturewere refluxed
  2. temperatureAfter refluxing
  3. temperatureto cool
  4. extractionThe resultant aqueous solution was extracted twice with ether
  5. washThe combined ether fractions were washed once with 5% aqueous sodium hydroxide and 4 times with water
  6. dry with materialThe washed ether fractions were then dried
  7. filtrationfiltered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-29e56ed1af5a42a48abec3c0070f1d8e
Source dataset
uspto-grants-1991_12
Patent number
US05071862

Reaction notes

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