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

HRID 1758

反応式

HRID 1758 の反応式
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][CH3:28])(=[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][CH3:28])=[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

参加物

8

反応物 3

HCID 7294Methyl AcrylateHCID 517044Potassium AcetateHCID 196927132-Bromo-3-benzyloxy-6-hydroxymethylpyridine

生成物 1

HCID 86751043Methyl (3-benzyloxy-6-hydroxymethylpyridin-2-yl)propenoate収率 84.1%

試薬・触媒・溶媒 4

HCID 67553Tetrabutylammonium Iodide触媒HCID 178418476HCID 178418476、化合物触媒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 2-bromo-3-benzyloxy-6-hydroxymethylpyridine (2.94 g, 10 mmol) in DMF (19 ml) and water (1 ml) were added potassium acetate (2.45 g, 10.0 mmol), tetra-n-butylammonium iodide (3.69 g. 10.0 mmol), bis(triphenyl-phosphine)palladium dichloride (281 mg, 0.4 mmol) and methyl acrylate (2.70 ml. 2.58 g, 30 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 5 h. The mixture was cooled and added to 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. The residue was purified by flash column chromatography eluting with dichloromethane, then 4:1 dichloromethane:ethyl acetate to give the product (2.516 g, 84%).

後処理

  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. customThe residue was purified by flash column chromatography
  7. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-a748f251ca1d423aa7e17eaf3d09ac7f
出典データセット
uspto-grants-1998_03
特許番号
US05726315

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