Triethylamine → (4-tert-Butyl-2-nitro-phenylethynyl)-trimethyl-silane

HRID 600353Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8](OS(C(F)(F)F)(=O)=O)=[C:7]([N+:19]([O-:21])=[O:20])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31]>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.CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])=[C:7]([N+:19]([O-:21])=[O:20])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To Trifluoro-methanesulfonic acid 4-tert-butyl-2-nitro-phenyl ester (3.715 g, 11.35 mmol), dichlorobis(triphenylphosphine)palladium(II) (336 mg, 0.478 mmol), cuprous iodide (168 mg, 0.882 mmol) was added dimethylformamide (45 mL), triethylamine (1.72 g, 17.0 mmol), and trimethylsilylacetylene (2.229 g, 22.70 mmol). The resulting mixture was heated at 90° C. under an atmosphere of nitrogen for 15 minutes. This was partitioned between ethylacetate and water. The ethylacetate layer was washed with brine, dried over anhydrous MgSO4, concentrated in vacuo, and purified by flash chromatography with elution with CH2Cl2 to yield (4-tert-Butyl-2-nitro-phenylethynyl)-trimethyl-silane (3.193 g, 11.61 mmol).

Workup

customThis was partitioned between ethylacetate and water
washThe ethylacetate layer was washed with brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated in vacuo
custompurified by flash chromatography with elution with CH2Cl2

Sources & evidence

ORD record: ord-d83ef3e75dc34058990af5048c08266f
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902194B2

Reaction notes

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