Water → HCID 13417266, compound

HRID 1284461Notes

Reaction equation

HRID 1284461 reaction equation
[H-].[Na+].[Br-].[C:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[C:36]([C:44]1[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=1)(=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O>CCCCCC.CS(C)=O>[C:37]1(/[C:36](/[C:44]2[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=2)=[CH:16]/[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:4]([OH:6])=[O:5])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 962WaterHCID 21540Phenyl-3-pyridinylmethanoneHCID 24758Sodium hydrideHCID 11432504Phosphonium, (10-carboxydecyl)triphenyl-, bromide

Product 1

HCID 13417266HCID 13417266, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
85 °C

Procedure

Sodium hydride (60% dispersion in oil, 2.7 g, 68 mmoles) was washed with hexane and, after removal of the hexane under reduced pressure, dimethyl sulfoxide (40 ml) was added and the mixture was stirred with heating at 85° C. for an hour. After cooling, a dimethyl sulfoxide solution (20 ml) containing 10-carboxydecyltriphenylphosphonium bromide (18.0 g, 34 mmoles) was added dropwise to the mixture. After 10 minutes, a solution of 3-benzoylpyridine (6.2 g, 33.8 mmoles) in dimethyl sulfoxide (10 ml) was added. The reaction was allowed to proceed for an hour and, following addition of water (200 ml), the reaction product was washed with toluene. The aqueous layer was acidified with 2N hydrochloric acid to pH 5.2, and the product was extracted with ethyl acetate. The organic layer was washed with water, dried and distilled under reduced pressure to remove the solvent. The residue was then subjected to silica gel column chromatography using ethyl acetate as the developing solvent to give (Z)-12-phenyl-12 -(3-pyridyl)-11-dodecenoic acid (Compound Id-8, 3.2 g), after fractional recrystallization from isopropylether.

Workup

  1. customafter removal of the hexane under reduced pressure, dimethyl sulfoxide (40 ml)
  2. additionwas added
  3. temperatureAfter cooling
  4. additionwas added dropwise to the mixture
  5. waitto proceed for an hour
  6. washthe reaction product was washed with toluene
  7. extractionthe product was extracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. customdried
  10. distillationdistilled under reduced pressure
  11. customto remove the solvent

Sources & evidence

ORD record
ord-443bd2d8607543198f2d7ad6bc89eb33
Source dataset
uspto-grants-1986_01
Patent number
US04563446

Reaction notes

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