Triphenylphosphine → 3-{6-Hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridin-2-yl}propenoic Acid

HRID 264786

Reaction equation

HRID 264786 reaction equation
Br[C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:6][CH:5]=[C:4]([CH2:25][OH:26])[N:3]=1.C([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:51]([O-:55])(=[O:54])[CH:52]=[CH2:53].[K+]>CN(C=O)C.O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Pd](Cl)Cl>[OH:26][CH2:25][C:4]1[N:3]=[C:2]([CH:53]=[CH:52][C:51]([OH:55])=[O:54])[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:6][CH:5]=1

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 4429391Potassium acrylate2×HCID 196927112-Bromo-6-hydroxymethyl-[8(4-methoxyphenyl)octyloxy]pyridine

Product 1

HCID 540218973-{6-Hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridin-2-yl}propenoic Acid

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-bromo-6-hydroxymethyl-[8(4-methoxyphenyl)octyloxy]pyridine (5.00 g, 11.8 mmol) in DMF (22.8 ml) and water (1.2 ml) were added potassium acetate (2.91 g, 29.7 mmol), tetra-n-butylammonium iodide (4.37 g, 11.8 mmol), triphenylphosphine (0,245 g, 0.94 mmol), palladium chloride (83 mg, 0.47 mmol) and potassium acrylate (3.91 g, 35.4 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 3.3 h. Some potassium acrylate remained undissolved. The mixture was cooled, solids filtered and washed with ethyl acetate (2×60 ml). The filtrate was washed with water (250 ml) and with 5% sodium chloride solution (2×125 ml). The organic layer was dried and evaporated. The pure product was obtained by flash column chromatography (silica, 2,0% ether in dichloromethane) (3.52 g, 72%). mp 112°114° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationsolids filtered
  3. washwashed with ethyl acetate (2×60 ml)
  4. washThe filtrate was washed with water (250 ml) and with 5% sodium chloride solution (2×125 ml)
  5. customThe organic layer was dried
  6. customevaporated
  7. customThe pure product was obtained by flash column chromatography (silica, 2,0% ether in dichloromethane) (3.52 g, 72%)
  8. custommp 112°114° C.

Sources & evidence

ORD record
ord-ea78dff7ba164da1b7519d695e39162b
Source dataset
uspto-grants-1997_07
Patent number
US05646286

Linked notes

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