Tetrahydrofuran → HCID 86693799, compound

HRID 1627719Notes

Reaction equation

O1CCCC1.C(N(CC)CC)C.[C:13]([C:17]#[CH:18])([CH3:16])([CH3:15])[CH3:14].[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][C:13]([CH3:16])([CH3:15])[CH3:14])[C:24]([CH3:28])=[CH:23][C:21]=1[NH2:22]

Participants

Conditions

Temperature: 50 °C

Procedure

Tetrahydrofuran (5 ml), 5 ml of triethylamine, 216 mg of tert-butylacetylene, 71 mg of palladium chloride-ditriphenylphosphine complex, and 19 mg of copper iodide were added to 0.5 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=10:1), thereby obtaining 0.31 g of 2,5-dimethyl-4-(3,3-dimethyl-1-butynyl)aniline (Compound 4-25).

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=10:1)

Sources & evidence

ORD record: ord-1245c12a718e4690b1cc4fad15ca60b7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785649B2

Reaction notes

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