1-Pentyne → Ethyl (3-(pentyne-1-yl)phenyl)acetate

HRID 59021

Reaktionsgleichung

[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:33]#[C:34][CH2:35][CH2:36][CH3:37]>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.O>[C:33]([C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])[CH:11]=[CH:10][CH:9]=1)#[C:34][CH2:35][CH2:36][CH3:37]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of ethyl(3-bromophenyl)acetate (0.3 g, 1.24 mmol) and tetrabutylammonium fluoride hydrate (0.97 g, 3.72 mmol), was treated with PdCl2(PPh3)2 (26 mg, 0.037 mmol; 3 mole %) and 1-pentyne (367 μL, 3.72 mmol) in a sealed tube. The tube was heated at 80° C. for 2 h. The mixture was treated with water, and was extracted with diethyl ether. The organic extract was dried over sodium sulfate, filtered and evaporated in vacuo to give the crude product. Purification on a Biotage™ 25 M column (silica), eluting with ethyl acetate/hexane 0:1 to 2:98, gave ethyl (3-(pentyne-1-yl)phenyl)acetate as a pale yellow oil (0.23 g, 79%).

Aufarbeitung

extractionwas extracted with diethyl ether
extractionThe organic extract
dry with materialwas dried over sodium sulfate
filtrationfiltered
customevaporated in vacuo
customto give the crude product
customPurification on a Biotage™ 25 M column (silica)
washeluting with ethyl acetate/hexane 0:1 to 2:98

Quellen und Nachweise

ORD-Eintrag: ord-88dbc1b4edb54ade9774a49832ce807e
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09439882B2

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