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

HRID 495279
ノート
印刷プレビュー

反応式

HRID 495279 の反応式
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][C:17]([O:19][CH3:20])=[O:18].[CH:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[CH:21]([C:23]1[CH:28]=[C:27]([C:2]2[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=2[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:26]=[CH:25][CH:24]=1)=[O:22]
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 3

HCID 10796Cesium carbonateHCID 27343563-Formylphenylboronic acidHCID 68420121Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate

生成物 1

HCID 86613495Methyl 2-(3-formylphenyl)-3,5-bis(methoxymethoxy)phenylacetate収率 75%

試薬・触媒・溶媒 3

HCID 178424406HCID 178424406、化合物触媒
HCID 962
Water
溶媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

Methyl 2-bromo-3,5-bis(methoxymethoxy)phenylacetate (630 mg, 1.8 mmol)-obtained in the step 2 in Example 1 was dissolved in a mixed solvent of 1,2-dimethoxyethane (10 mL) and water (2 mL), and in an argon atmosphere, 3-formylphenylboronic acid (400 mg, 2.7 mmol), bis(tri-o-tolylphosphine)palladium(II) dichloride (140 mg, 0.17 mmol) and cesium carbonate (1.1 g, 7.2 mmol) were added thereto, and stirred under heat for 10 hours. The reaction mixture was cooled to room temperature, then filtered, and the filtrate was concentrated under reduced pressure. Water was added to the resulting residue, and extracted twice with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/4 to 1/2) to obtain methyl 2-(3-formylphenyl)-3,5-bis(methoxymethoxy)phenylacetate (500 mg, 75%).

後処理

  1. temperatureunder heat for 10 hours
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the resulting residue
  5. extractionextracted twice with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate/n-hexane=1/4 to 1/2)

出典と根拠

ORDレコード
ord-8cf20890d64e481aa77ccce4a57d86a9
出典データセット
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07538241B2

反応ノート

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