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

HRID 734993Notes

Reaction equation

HRID 734993 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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)).

Workup

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

Sources & evidence

ORD record
ord-8f5608e81c4f485385c956a0f3073e6d
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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