Water → 2'-Methoxy-4'-(thien-2-yl)acetophenone

HRID 1792971

反応式

HRID 1792971 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][C:5]=1[C:8](=[O:10])[CH3:9]

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 220255511-(4-Iodo-2-methoxyphenyl)ethanone

生成物 1

HCID 219810692'-Methoxy-4'-(thien-2-yl)acetophenone収率 98%

試薬・触媒・溶媒 2

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

実験手順

Ex-57a: 4′-iodo-2′-methoxyacetophenone (1.08 g, 3.9 mmol) in ethylene glycol dimethyl ether (50 ml) was degassed for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.456 g, 0.39 mmol), thiophene-2-boronic acid (0.75 g, 5.9 mmol), and sodium carbonate solution (2 m, 4 ml, 8 mmol) were added. The mixture was stirred at reflux under nitrogen for 24 hours. Upon cooling to room temperature, it was poured into water and extracted with dichloromethane. The organic phase was dried over sodium sulfate and evaporated. Silica gel chromatography (hexane/ethyl acetate, 3:1) gave 0.88 g (98%) of the desired 2′-methoxy-4′-(thien-2-yl)acetophenone.

後処理

  1. temperatureat reflux under nitrogen for 24 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated

出典と根拠

ORDレコード
ord-754c7a9dc18444ce999681af4bf22fa9
出典データセット
uspto-grants-2006_07
特許番号
US07078431B2

関連ノート

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