Trimethylsilylacetylene → [4-(1-Ethoxycyclopropyl)-3-tert-butyl-phenylethynyl]-trimethylsilane

HRID 2299454Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2([O:16][CH2:17][CH3:18])[CH2:15][CH2:14]2)=[C:9]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:8]=1)(=O)=O.[CH3:25][Si:26]([C:29]#[CH:30])([CH3:28])[CH3:27]>C(N(CC)CC)C.CN(C=O)C.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>[CH2:17]([O:16][C:13]1([C:10]2[CH:11]=[CH:12][C:7]([C:30]#[C:29][Si:26]([CH3:28])([CH3:27])[CH3:25])=[CH:8][C:9]=2[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]1)[CH3:18]

Participants

Conditions

Temperature: 95 °C

Procedure

Using General Procedure D; 4-(1-ethoxycyclopropyl)-3-tert-butyl-phenyl 1,1,1-trifluoromethansulfonate (Intermediate 110, 260.0 mg, 0.71 mmol) in triethylamine (4 mL) and DMF (6 mL) was sparged with argon for 5 minutes. Trimethylsilylacetylene (0.70 g, 7.1 mmols) was then added followed by dichlorobis-(triphenylphosphine)palladium(II) (40.0 mg, 0.06 mmol). The resulting reaction mixture was heated to 95° C. for 18 hours. The title compound, 215.0 mg (96%), was isolated by chromatography (0-2% EtOAc-hexanes) as an orange oil.

Workup

customThe resulting reaction mixture

Sources & evidence

ORD record: ord-6a5c89497f684cd19012b0b23ebc5721
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495552B2

Reaction notes

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