Triethylamine → HCID 57424257, compound

HRID 2377456Notes

Reaction equation

HRID 2377456 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=1)([CH3:7])[CH3:6])[CH3:2].C(N(CC)CC)C.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25].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>[CH2:1]([O:3][C:4](=[O:15])[C:5]([CH3:7])([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])[CH:9]=1)[CH3:6])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 12805127Ethyl 2-(3-bromophenyl)-2-methylpropanoate2×

Product 1

HCID 57424257HCID 57424257, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent2×

Procedure

Following General Procedure D and using 2-(3-bromo-phenyl)-2-methyl-propionic acid ethyl ester (Intermediate 130, 0.77 g, 2.84 mmol), triethyl amine (5 mL), copper(I)iodide (0.044 g, 0.23 mmol), trimethylsilyl acetylene (2 mL, 14.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.159 g, 0.23 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane to 5% ethyl acetate in hexane as the eluent, the title compound (0.74 g, 90%) was obtained as an orange oil.

Sources & evidence

ORD record
ord-98038cd9aad14d618062386e82012f35
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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