Ethyl Acrylate → ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate

HRID 226357

反応式

HRID 226357 の反応式
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](I)=[CH:4][N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C.[C:41]([O:45][CH2:46][CH3:47])(=[O:44])[CH:42]=[CH2:43]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:1][C:2]1[N:3]=[CH:4][C:5](/[CH:43]=[CH:42]/[C:41]([O:45][CH2:46][CH3:47])=[O:44])=[CH:6][C:7]=1[CH3:8]

参加物

8

反応物 4

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 101086802-Bromo-5-iodo-3-methylpyridine

生成物 1

HCID 86603663ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 2-bromo-5-iodo-3-methylpyridine (1.5 g) in DMF (15 mL) was added palladium(II) acetate (56.5 mg) and tri-o-tolylphosphine (230 mg) and diisopropylethylamine (3.5 mL), and ethyl acrylate (1.09 mL). The mixture was heated at 90° C. for 1 hour. Resulting mixture was poured into water and extracted with AcOEt. The organic layer was washed with water and brine, and dried over Na2SO4, and the solvent was removed in vacuo. Residual brown oil was purified by silica gel column chromatography eluted with AcOEt and hexane (1:4-1:2) to give ethyl (2E)-3-(6-bromo-5-methyl-3-pyridyl)acrylate (1.00 g) as pale yellow powder.

後処理

  1. customResulting mixture
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was removed in vacuo
  6. customwas purified by silica gel column chromatography
  7. washeluted with AcOEt and hexane (1:4-1:2)

出典と根拠

ORDレコード
ord-1526812b5b584f43bb9038b3b0fb20ce
出典データセット
uspto-grants-2009_07
特許番号
US07557127B2

関連ノート

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