Water → N-[2-(3,3-dimethylbut-1-ynyl)phenyl]acetamide

HRID 1359946ノート

反応式

HRID 1359946 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6].[CH3:12][C:13]([CH3:17])([CH3:16])[C:14]#[CH:15].O>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:12][C:13]([CH3:17])([CH3:16])[C:14]#[C:15][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6]

参加物

7

反応物 3

HCID 962WaterHCID 135123,3-Dimethyl-1-butyneHCID 1364162'-Bromoacetanilide

生成物 1

HCID 58792458N-[2-(3,3-dimethylbut-1-ynyl)phenyl]acetamide収率 100.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
50 °C

実験手順

Under argon, 25.7 g (120 mmol) of ortho-bromoacetanilide, 5.05 g (7.2 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1.37 g (7.2 mmol) of copper(I) iodide were initially charged in 450 ml of triethylamine. At room temperature, 17.8 g (180 mmol) of 3,3-dimethyl-1-butyne were then added dropwise over a period of 10 min, and the mixture is stirred at 50° C. for 5 h. The reaction mixture was poured into 2 l of water and extracted 3 times with in each case 250 ml of diethyl ether, and the extracts were dried over sodium sulphate and concentrated. Column-chromatographic purification on silica gel 60 with methylene chloride gave 25.9 g of N-[2-(3,3-dimethylbut-1-ynyl)-phenyl]acetamide of logP (pH 2.3)=3.03.

後処理

  1. extractionextracted 3 times with in each case 250 ml of diethyl ether
  2. dry with materialthe extracts were dried over sodium sulphate
  3. concentrationconcentrated
  4. customColumn-chromatographic purification on silica gel 60 with methylene chloride

出典と根拠

ORDレコード
ord-0061bc25fdb74472bde1c4694bd5b609
出典データセット
uspto-grants-2011_02
特許番号
US07879760B2

反応ノート

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