Diethyl Ether → t-Butyl 3-{6-hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridin-2-yl}propenoate

HRID 1752

Reaktionsgleichung

Reaktionsgleichung von HRID 1752
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+].[C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:35])[CH:33]=[CH2:34].CCOCC>CN(C=O)C.O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:26][CH2:25][C:4]1[N:3]=[C:2]([CH:34]=[CH:33][C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[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

Komponenten

10

Edukt 4

HCID 3283Diethyl EtherHCID 15458tert-Butyl acrylateHCID 517044Potassium AcetateHCID 196927112-Bromo-6-hydroxymethyl-[8(4-methoxyphenyl)octyloxy]pyridine

Produkt 1

HCID 54231524t-Butyl 3-{6-hydroxymethyl-3-[8(4-methoxyphenyl)octyloxy]pyridin-2-yl}propenoate

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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 (3.00 g, 30.6 mmol), tetra-n-butylammonium iodide (4.36 g, 11.8 mmol), bis(triphenylphosphine)palladium dichloride (0.33 g, 0.47 mmol) and t-butyl acrylate (6.16 g, 48 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 45 min. The mixture was cooled and added to water (250 ml). The product was extracted into ethyl acetate (2×60 ml). The combined extracts were washed with water (100 ml), 5% sodium chloride solution (2×100 ml), then dried and evaporated. The product was obtained by flash column chromatography using silica and 10% ether in dichloromethane. Yield 4.29 g, 77%.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionThe product was extracted into ethyl acetate (2×60 ml)
  3. washThe combined extracts were washed with water (100 ml), 5% sodium chloride solution (2×100 ml)
  4. customdried
  5. customevaporated
  6. customThe product was obtained by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-518c5ae80b704ac1999ffc9853c652ad
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726315

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