Ethyl Acrylate → Ethyl (3-hydroxy-6-methylpyridin-2-yl)propenoate

HRID 1754

반응식

HRID 1754 반응식
[OH:1][C:2]1[C:3](I)=[N:4][C:5]([CH3:8])=[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:34]([O:38][CH2:39][CH3:40])(=[O:37])[CH:35]=[CH2:36]>CN(C=O)C.O.[Pd](Cl)Cl>[OH:1][C:2]1[C:3]([C:35](=[CH2:36])[C:34]([O:38][CH2:39][CH3:40])=[O:37])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 899572-Iodo-6-methylpyridin-3-olHCID 517044Potassium Acetate

생성물 1

HCID 131720091Ethyl (3-hydroxy-6-methylpyridin-2-yl)propenoate

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

To a solution of 3-hydroxy-2-iodo-6-methylpyridine (1.175 g, 5.0 mmol) in DMF (9.5 ml) and water (0.5 ml) were added potassium acetate (1.23 g, 12.5 mmol), triphenylphosphine (105 mg, 0.40 mmol), palladium chloride (36 mg, 0.20 mmol) and ethyl acrylate (1.63 ml, 1.50 g, 15.0 mmol). The mixture was placed under nitrogen and heated at 120° C. for 1.5 h. The mixture was cooled, filtered from deposited palladium black, and added to water (100 ml). The product was extracted into ethyl acetate (3×30 ml). The combined extracts were washed with water (2×25 ml) and with brine (25 ml), then dried over sodium sulphate and evaporated. This left a tan solid, the product (951 mg, 91%). mp 192°-195° C. (dec)

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. additionadded to water (100 ml)
  4. extractionThe product was extracted into ethyl acetate (3×30 ml)
  5. washThe combined extracts were washed with water (2×25 ml) and with brine (25 ml)
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. waitThis left a tan solid

출처 및 근거

ORD 기록
ord-daea2679130c4e96a69efc91647c4537
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726315

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