Tetrahydrofuran → HCID 86693800, compound

HRID 1627720Notes

Reaction equation

O1CCCC1.C(N(CC)CC)C.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].[CH3:19][C:20]1[CH:26]=[C:25](I)[C:24]([CH3:28])=[CH:23][C:21]=1[NH2:22]>[Cu](I)I.C(OCC)(=O)C.O>[CH3:19][C:20]1[CH:26]=[C:25]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[C:24]([CH3:28])=[CH:23][C:21]=1[NH2:22]

Participants

Conditions

Temperature: 50 °C

Procedure

Tetrahydrofuran (100 ml), 100 ml of triethylamine, 7.6 g of trimethylsilyl acetylene, 1.25 g of palladium chloride-ditriphenylphosphine complex, and 0.34 g of copper iodide were added to 14.7 g of 2,5-dimethyl-4-iodoaniline, and the mixture was stirred at 50° C. for 15 hours. After completion of the reaction, water was added to the reaction solution, and extraction was performed 3 times with ethyl acetate. The organic layer was collected, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), thereby obtaining 9.8 g of 2,5-dimethyl-4-(2-trimethylsilyl-1-ethynyl)aniline (Compound 4-27).

Workup

additionwas added to the reaction solution, and extraction
customThe organic layer was collected
washwashed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-1ab58dd2fea2479f97d59f19d9de0376
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785649B2

Reaction notes

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