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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
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HRID 1920785 반응식
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]
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참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

(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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-2d9a8dc812324c9194ab9a74d6cc62d6
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173631B2

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