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

HRID 1755
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HRID 1755 반응식
[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
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참가 물질

8

반응물 4

HCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 196927093-Hydroxy-6-hydroxymethyl-2-iodopyridine

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate
촉매
HCID 962Water용매2회
HCID 6228Dimethylformamide용매

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, 7.5 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.

후처리

  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.

출처 및 근거

ORD 기록
ord-33f5c2c61cec497c9cae12b9bafc104f
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05726315

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