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

HRID 264788

반응식

HRID 264788 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-4b2390ef96a742d7bbc32ccde24cd73d
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646286

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