Triethylamine → (3-tert-Butyl-phenylethynyl)-trimethyl-silane

HRID 1765811Notes

Reaction equation

HRID 1765811 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=1)(=O)=O.C(N(CC)CC)C.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28].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>[C:13]([C:9]1[CH:8]=[C:7]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])[CH:12]=[CH:11][CH:10]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 22261847HCID 22261847, compound

Product 1

HCID 14989665(3-tert-Butyl-phenylethynyl)-trimethyl-silane

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 D and using trifluoromethanesulfonic acid, 3-tert-butyl-phenyl ester (Intermediate-101, 2.54 g, 0.9.0 mmol), triethyl amine (2 mL), copper(I)iodide (0.63 g, 3.33 mmol), trimethylsilyl acetylene (5 mL, 36 mmol) and, dichlorobis(triphenylphosphine)palladium(II) (1.6 g, 2.25 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 10% ethyl acetate in hexane as the eluent, the title compound was obtained as a brown oil that was used as such for the next step.

Sources & evidence

ORD record
ord-1f144dd2474a40e7825df036651384a6
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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