Diethyl Ether → (E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-5-[3-(3-thienyl)phenoxy]-4-oxopentylamine

HRID 1464739Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][C:5](=[O:19])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:9]=1.Cl.[CH2:21]([NH:23][CH2:24]/[CH:25]=[CH:26]/[C:27]#[C:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:22].[I-].[K+].C(OCC)C>CN(C)C=O>[CH2:21]([N:23]([CH2:2][CH2:3][CH2:4][C:5](=[O:19])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH:9]=1)[CH2:24]/[CH:25]=[CH:26]/[C:27]#[C:28][C:29]([CH3:30])([CH3:32])[CH3:31])[CH3:22]

Participants

Conditions

Temperature: 40 °C

Procedure

50 mg of 5-bromo-1-[3-(3-thienyl)phenoxy]-2-pentanone was dissolved in 1.8 ml of dimethylformamide, and 125 mg of a (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine hydrochloride and 29 mg of potassium iodide were added. The mixture was stirred at 40° C. for 1 hour, and then ethyl ether and ice water were added. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [hexane→chloroform] to give 20 mg (yield 27%) of the captioned compound as a colorless oil.

Workup

customThe organic layer was separated
washwashed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customThe desiccant was separated by filtration
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography [hexane→chloroform]

Sources & evidence

ORD record: ord-bec18076e81d4c15b454886083fdc14f
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05306728

Reaction notes

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