Propargyl alcohol → 3-(4-Nitrophenyl)prop-2-yn-1-ol

HRID 24931

反応式

HRID 24931 の反応式
[CH2:1]([OH:4])[C:2]#[CH:3].C(N(CC)CC)C.Br[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>C(#N)C.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].[Cu]I>[OH:4][CH2:1][C:2]#[C:3][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1

参加物

8

反応物 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 114661-Bromo-4-nitrobenzene

生成物 1

HCID 50337133-(4-Nitrophenyl)prop-2-yn-1-ol

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

8.55 g (0.15 mol) of propargyl alcohol and 152 ml (110 g, 1.09 mol) of triethylamine are added to a solution of 20.2 g (0.1 mol) of 4-bromonitrobenzene in 285 ml of acetonitrile. The reaction solution is heated to 100° C. 11.9 g (10 mmol) of Pd(Pph3)4 and 3.94 g (20 mmol) of copper (I) iodide are added. After 10 minutes the solvent is eliminated in vacuo and the residue taken up in ethyl acetate. It is washed with water and ammonia water, filtered through Celite and the solvent is eliminated in vacuo. The product is obtained by chromatography on silica gel (dichloromethane/methanol=10:1).

後処理

  1. washIt is washed with water and ammonia water
  2. filtrationfiltered through Celite
  3. customThe product is obtained by chromatography on silica gel (dichloromethane/methanol=10:1)

出典と根拠

ORDレコード
ord-7d8c42409bc3412a8e79172bc76b0462
出典データセット
uspto-grants-2005_02
特許番号
US06855710B2

関連ノート

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