Triethylamine → HCID 60029385, compound

HRID 2377472Notes

Reaction equation

HRID 2377472 reaction equation
[C:1]([C:5]1[C:6]([O:16][CH:17]([CH3:19])[CH3:18])=[C:7]([C:10]([CH3:15])=[C:11]([C:13]#[CH:14])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:20][O:21][C:22](=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=1.C(N(CC)CC)C.C(OCC)(=O)C>CCCCCC.[Cu]I.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>[CH3:20][O:21][C:22](=[O:31])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:14]#[C:13][C:11]2[CH:12]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([O:16][CH:17]([CH3:19])[CH3:18])=[C:7]([CH:8]=[O:9])[C:10]=2[CH3:15])=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10378700Methyl 4-IodophenylacetateHCID 211071573-tert-Butyl-5-ethynyl-2-isopropoxy-6-methyl-benzaldehyde2×

Product 1

HCID 60029385HCID 60029385, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure B and using 3-tert-butyl-5-ethynyl-2-isopropoxy-6-methyl-benzaldehyde (Intermediate 143, 0.35 g, 1.35 mmol), 4-iodo phenyl acetic acid methyl ester (0.374 g, 1.35 mmol), triethyl amine (8 mL), copper(I)iodide (0.02 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.072 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 3-5% ethyl acetate in hexane as the eluent, the title compound was obtained as a white solid (0.37 g, 75%).

Sources & evidence

ORD record
ord-fc7c30afe40d49469ace288c3bda3b31
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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