Propargyl alcohol → HCID 67539293, compound

HRID 2241014Notes

Reaction equation

HRID 2241014 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:21])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH2:22]([OH:25])[C:23]#[CH:24].C(N(CC)CC)C>CC#N.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>[F:19][CH:18]([F:20])[O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9](=[O:10])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:24]#[C:23][CH2:22][OH:25])[CH:3]=2)=[O:21])=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 59790342HCID 59790342, compound

Product 1

HCID 67539293HCID 67539293, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(3-bromophenyl)-2-(4-(difluoromethoxy)phenyl)ethane-1,2-dione (0.500 g, 1.41 mmol), prop-2-yn-1-ol (0.395 g, 7.04 mmol), bis(triphenylphosphine)palladium(II) chloride (0.099 g, 0.14 mmol), copper(I) iodide (0.021 g, 0.11 mmol) and triethylamine (0.62 g, 6.11 mmol) in CH3CN (3 mL) was stirred at 60° C. overnight. The solvent is removed and the material is absorbed onto celite and purified by flash chromatography (silica, 25:75 ethyl acetate/hexanes) to afford 1-(4-(difluoromethoxy)phenyl)-2-(3-(3-hydroxyprop-1-ynyl)phenyl)ethane-1,2-dione (0.326 g, 70%) as an off white solid.

Workup

  1. customThe solvent is removed
  2. customthe material is absorbed onto celite
  3. custompurified by flash chromatography (silica, 25:75 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-066c4bfe1fb048a08a529acc4ec16a39
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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