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

HRID 734993노트

반응식

HRID 734993 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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)).

후처리

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

출처 및 근거

ORD 기록
ord-8f5608e81c4f485385c956a0f3073e6d
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592373B2

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