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Sodium Carbonate → 4-(3-Chloro-5-vinylpyridin-2-yl)benzaldehyde

HRID 1430095
ノート
印刷プレビュー

反応式

HRID 1430095 の反応式
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].Cl[C:19]1[C:24]([Cl:25])=[CH:23][C:22]([CH:26]=[CH2:27])=[CH:21][N:20]=1>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:25][C:24]1[C:19]([C:12]2[CH:13]=[CH:14][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=2)=[N:20][CH:21]=[C:22]([CH:26]=[CH2:27])[CH:23]=1
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 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 574168492,3-Dichloro-5-ethenylpyridine

生成物 1

HCID 578256984-(3-Chloro-5-vinylpyridin-2-yl)benzaldehyde収率 94.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒
HCID 962
Water
溶媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

4.1 g of Na2CO3 (39 mmol), 2.0 g of 4-formylphenylboronic acid (13 mmol), and 0.45 g of Pd(PPh3)4 were added to 2.5 g of compound (8) (14.9 mmol) prepared in Example 5 dissolved in 50 mL of 1,2-dimethoxyethane and 50 mL of distilled water, and refluxed under heating and stirring for 18 hours. The mixture was cooled to room temperature, and concentrated about 50% under reduced pressure. The aqueous layer was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: ethyl acetate/hexane=1/4) to obtain 3.0 g 4-(3-chloro-5-vinylpyridin-2-yl)benzaldehyde (yield 82%).

後処理

  1. temperatureunder heating
  2. concentrationconcentrated about 50% under reduced pressure
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated by column chromatography (eluting solvent: ethyl acetate/hexane=1/4)

出典と根拠

ORDレコード
ord-e9e04adaffb047cfb998a9f4402c8c8d
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08940769B2

反応ノート

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