Butyl Acrylate → n-Butyl (3-benzyloxy-6-hydroxymethylpyridin-2-yl)propenoate

HRID 1757

반응식

HRID 1757 반응식
Br[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[C:4]([CH2:16][OH:17])[N:3]=1.C([O-])(=O)C.[K+].[C:23]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])(=[O:26])[CH:24]=[CH2:25]>CN(C=O)C.O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:9]([O:8][C:7]1[C:2]([C:24](=[CH2:25])[C:23]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26])=[N:3][C:4]([CH2:16][OH:17])=[CH:5][CH:6]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

8

반응물 3

HCID 8846Butyl AcrylateHCID 517044Potassium AcetateHCID 196927132-Bromo-3-benzyloxy-6-hydroxymethylpyridine

생성물 1

HCID 86751042n-Butyl (3-benzyloxy-6-hydroxymethylpyridin-2-yl)propenoate

시약·촉매·용매 4

HCID 67553Tetrabutylammonium Iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매2회HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

To a solution of 2-bromo-3-benzyloxy-6-hydroxymethylpyridine (2.94 g, 10.0 mmol) in DMF (19 ml) and water (1 ml) were added potassium acetate (2.45 g, 25.0 mmol), tetra-n-butylammonium iodide (3.69 g, 10.0 mmol), bis(triphenylphosphine)palladium dichloride (281 mg, 0.4 mmol) and n-butyl acrylate (4.31 ml, 3.84 g, 30 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 3 h. The mixture was cooled and poured into water (180 ml). The product was extracted into ethyl acetate (3×30 ml). The combined extracts were washed with water (3×25 ml), dried and evaporated. This residue was purified by flash column chromatography, eluting with a gradient of ethyl acetate in dichloromethane to isolate the product, an oil (2.72 g, 80%).

후처리

  1. temperatureThe mixture was cooled
  2. extractionThe product was extracted into ethyl acetate (3×30 ml)
  3. washThe combined extracts were washed with water (3×25 ml)
  4. customdried
  5. customevaporated
  6. customThis residue was purified by flash column chromatography
  7. washeluting with a gradient of ethyl acetate in dichloromethane
  8. customto isolate the product

출처 및 근거

ORD 기록
ord-cbc402db79bd4ddea3a7284194868b01
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726315

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