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Ethyl Acrylate → Ethyl (2E)-3-(2-methyl-6-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)prop-2-enoate

HRID 1920785
ノート
印刷プレビュー

反応式

HRID 1920785 の反応式
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]([O:11][CH2:12][C@H:13]1[CH2:15][O:14]1)[CH3:10].[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH:17]=[CH2:18].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+].C(#N)CC.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C@H:9]([O:11][CH2:12][C@H:13]2[CH2:15][O:14]2)[CH3:10])[C:2]=1/[CH:18]=[CH:17]/[C:16]([O:20][CH2:21][CH3:22])=[O:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 8821Ethyl AcrylateHCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 58572531(2R)-2-{[(1R)-1-(2-Bromo-3-methylphenyl)ethoxy]methyl}oxiraneHCID 129718070Propionitrile water

生成物 1

HCID 58572472Ethyl (2E)-3-(2-methyl-6-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)prop-2-enoate
収率 63%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

実験手順

(2R)-2-{[(1R)-1-(2-Bromo-3-methylphenyl)ethoxy]methyl}oxirane (1505 mg, 5.57 mmol), which had been obtained in Example 3 (3b), ethyl prop-2-enoate (910 μL, 8.36 mmol), palladium acetate (II) (126 mg, 0.56 mmol), tris(2-methylphenyl)phosphine (170 mg, 0.56 mmol), and potassium carbonate (1537 mg, 11.1 mmol) were suspended in a mixed solvent (27.5 mL) of propionitrile-water (2:1), and stirred with heating under reflux for 5 hours. The reaction solution was cooled to room temperature, filtered by using Millicup-LH, and washed with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. After that, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a pale yellow oily substance (1025 mg, yield 63%).

後処理

  1. temperaturewith heating
  2. temperatureunder reflux for 5 hours
  3. filtrationfiltered
  4. washwashed with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter that, the solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-2d9a8dc812324c9194ab9a74d6cc62d6
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08173631B2

反応ノート

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