Dimethylformamide → Ethyl 3-{3-hydroxy-6-hydroxymethylpyridin2-yl}propenoate

HRID 264788

Reaktionsgleichung

[OH:1][C:2]1[C:3](I)=[N:4][C:5]([CH2:8][OH:9])=[CH:6][CH:7]=1.[C:11]([O-:14])(=[O:13])[CH3:12].[K+].[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:17]=1.[CH3:35]N(C=O)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:1][C:2]1[C:3]([CH:35]=[CH:12][C:11]([O:14][CH2:16][CH3:17])=[O:13])=[N:4][C:5]([CH2:8][OH:9])=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a solution of 3-hydroxy-6-hydroxymethyl-2-iodopyridine (708 mg, 2.82 mmol) in DMF (5.7 ml) and water (0.3 ml) were added potassium acetate (0.74 g, 7.5mmol), triphenylphosphine (63 mg, 0.24 mmol), ethyl amylate (0.98 ml, 0.90g, 9.0 mmol) and palladium acetate (27 mg, 0.12 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 5 h. The mix was cooled and poured into water (50 ml). The product was extracted into ethyl acetate (3×20ml) and the combined extracts were washed with water (2×15 ml) with brine (15 ml), dried and evaporated. The crude product was purified by passage in ethyl acetate through a pad of silica, yielding after evaporation a yellow solid (295 g, 47%). mp (B.HCl) 199°-203° C.

Aufarbeitung

temperatureThe mix was cooled
extractionThe product was extracted into ethyl acetate (3×20ml)
washthe combined extracts were washed with water (2×15 ml) with brine (15 ml)
customdried
customevaporated
customThe crude product was purified by passage in ethyl acetate through a pad of silica
customyielding
customafter evaporation a yellow solid (295 g, 47%)
custommp (B.HCl) 199°-203° C.

Quellen und Nachweise

ORD-Eintrag: ord-4b2390ef96a742d7bbc32ccde24cd73d
Quelldatensatz: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05646286

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