Dimethylformamide → Ethyl 3-{3-hydroxy-6-hydroxymethylpyridin2-yl}propenoate
Reaction equation
[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]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
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.
Workup
- 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.
Sources & evidence
- ORD record
- ord-4b2390ef96a742d7bbc32ccde24cd73d
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05646286
Reaction notes
Loading…