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

HRID 264788

反応式

HRID 264788 の反応式
[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

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 196927093-Hydroxy-6-hydroxymethyl-2-iodopyridine

生成物 1

HCID 54362899Ethyl 3-{3-hydroxy-6-hydroxymethylpyridin2-yl}propenoate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回

反応条件

温度
120 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4b2390ef96a742d7bbc32ccde24cd73d
出典データセット
uspto-grants-1997_07
特許番号
US05646286

関連ノート

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