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

HRID 1755
ノート
印刷プレビュー

反応式

HRID 1755 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([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:35]([O:39][CH2:40][CH3:41])(=[O:38])[CH:36]=[CH2:37]>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:1][C:2]1[C:3]([CH:37]=[CH:36][C:35]([O:39][CH2:40][CH3:41])=[O:38])=[N:4][C:5]([CH2:8][OH:9])=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8821Ethyl AcrylateHCID 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 3

HCID 167845palladium(II) acetate
触媒
HCID 962Water溶媒2 回
HCID 6228Dimethylformamide溶媒

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, 7.5 mmol), triphenylphosphine (63 mg, 0.24 mmol), ethyl acrylate (0.98 ml, 0.90 g, 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 (3×20 ml) and the combined extracts were washed with water (2×15 ml) with brine (15 ml), dried and evaporated. The etude 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 (3×20 ml)
  3. washthe combined extracts were washed with water (2×15 ml) with brine (15 ml)
  4. customdried
  5. customevaporated
  6. customThe etude 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-33f5c2c61cec497c9cae12b9bafc104f
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05726315

反応ノート

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