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Cesium carbonate → Methyl 3,5-bis(methoxymethoxy)-2-phenylphenylacetate

HRID 495177
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HRID 495177 반응식
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6](Br)=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd][P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 78412Phenyl dihydrogen orthoborateHCID 68420121Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate

생성물 1

HCID 23116311Methyl 3,5-bis(methoxymethoxy)-2-phenylphenylacetate

시약·촉매·용매 2

HCID 178424408HCID 178424408, 화합물촉매
HCID 962
Water
용매

실험 절차

Methyl 3,5-bis(methoxymethoxy)-2-bromophenylacetate (15.0 g, 43.0 mmol) obtained in Example 3, Step 1 was dissolved in a mixed solvent of 1,2-dimethoxymethane (0.15 L) and water (6.0 mL). To the solution were added phenylboric acid (7.3 g, 60 mmol), bis(tri-o-tolylphosphine)palladium (II) dichloride (0.68 g, 0.86 mmol) and cesium carbonate (42 g, 0.13 mol) in an atmosphere of argon, followed by stirring for 16.5 hours under heating and reflux. After cooling to room temperature, the reaction mixture was filtered under reduced pressure, and the filtrate was concentrated under reduced pressure. To the resulting residue was added water (0.50 L), followed by extraction with ethyl acetate (0.40 L×2). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/3) to obtain a quantitative yield of methyl 3,5-bis(methoxymethoxy)-2-phenylphenylacetate.

후처리

  1. temperatureunder heating
  2. temperaturereflux
  3. filtrationthe reaction mixture was filtered under reduced pressure
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the resulting residue was added water (0.50 L)
  6. extractionfollowed by extraction with ethyl acetate (0.40 L×2)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/3)

출처 및 근거

ORD 기록
ord-53bd78ad67e3420da1d87b06773a6b3c
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07538224B2

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