Cesium carbonate → 3-(4-Hydroxymethylphenyl)propynoic acid (4-prop-1-ynylphenyl)amide

HRID 734993ノート

反応式

HRID 734993 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].I[C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1.[C:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:29])[C:27]#[CH:28])=[CH:21][CH:20]=1)#[C:17][CH3:18]>[Cu]I>[C:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:29])[C:27]#[C:28][C:8]2[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=2)=[CH:21][CH:20]=1)#[C:17][CH3:18]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 290124-Iodobenzyl alcoholHCID 86060737Propynoic acid-(4-prop-1-ynylphenyl)amide

生成物 1

HCID 688177323-(4-Hydroxymethylphenyl)propynoic acid (4-prop-1-ynylphenyl)amide

試薬・触媒・溶媒 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒

実験手順

40 mL of THF are degassed, combined with 2.62 g (8.03 mmol) of cesium carbonate and 4-iodobenzyl alcohol and again degassed. To this reaction mixture is added successively 138 mg (0.12 mmol) of tetrakistriphenylphosphine palladium, 53 mg (0.28 mmol) of copper (I) iodide, and 0.7 g (3.2 mmol) of propynoic acid-(4-prop-1-ynylphenyl)amide. The mixture is stirred for 24 hours at ambient temperature and the reaction mixture is then evaporated down. The purification of the residues is carried out by column chromatography on silica gel (eluant: dichloromethane/ethanol (60:1)). Yield: 0.5 g (57.8% of theory); C19H15NO2 (M=289.33); calc.: molecular ion peak (M+H)+: 290; found: molecular ion peak (M+H)+: 290; Rf value: 0.21 (silica gel, dichloromethane/ethanol (50:1)).

後処理

  1. custom40 mL of THF are degassed
  2. customagain degassed
  3. customthe reaction mixture is then evaporated down
  4. customThe purification of the residues

出典と根拠

ORDレコード
ord-8f5608e81c4f485385c956a0f3073e6d
出典データセット
uspto-grants-2009_09
特許番号
US07592373B2

反応ノート

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