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

HRID 1869944Notes

Reaction equation

HRID 1869944 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, compound2×

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-tertbutyl-phenyl ester (Intermediate 101, 2.54 g, 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-9bb0b0465e484062ae3d5d51a6b19f21
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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