Reaktion #341546

Reaktionsgleichung

but-3-ynylcarbamic acid benzyl ester

1,4-diiodobenzene

THF

→

[4-(4-Iodophenyl)but-3-ynyl]carbamic acid benzyl ester

Ausbeute 86.0%

product 210

Ausbeute 86.0%

Lösungsmittel

—

TBF

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe flask was then evacuated
2. 2
   workup.ADDITIONre-filled with Argon
3. 3
   workup.ADDITIONwas added dropwise over 6 hours
4. 4
   SonstigeThe newly formed reaction mixture
5. 5
   workup.STIRRINGwas further stirred at room temperature overnight
6. 6
   Filtrationfiltered
7. 7
   EinengenThe filtrate was concentrated
8. 8
   workup.DISSOLUTIONThe residue was re-dissolved in dichloromethane
9. 9
   Sonstigepurified by column chromatography
10. 10
    Wascheneluting with a mixture of ethyl acetate (0-12%) and hexanes (100-88%)

Vorschrift

To a mixture of anhydrous THF and triethylamine (24 mL, 2/1, v/v) were sequentially added 1,4-diiodobenzene (2.03 g, 6.15 mmol) and copper (1) iodide (0.094 g, 0.246 mmol). The mixture was stirred at room temperature for 15 min. The flask was then evacuated and re-filled with Argon. The procedure was repeated three more times to ensure no oxygen remained. The catalyst, dichlorobis(triphenylphosphine)palladium(II) (0.173 g, 0.246 mmol) was added into the mixture under Argon protection. The other starting material, but-3-ynylcarbamic acid benzyl ester (0.50 g, 2.46 mmol), dissolved in TBF (8 mL) was added dropwise over 6 hours. The newly formed reaction mixture was further stirred at room temperature overnight. The solid in the reaction mixture was vacuum filtered. The filtrate was concentrated. The residue was re-dissolved in dichloromethane and purified by column chromatography, eluting with a mixture of ethyl acetate (0-12%) and hexanes (100-88%) to afford the product 210 (0.852 g, 86%) as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 2.61 (t, J=6.4 Hz, 2H), 3.44 (t, J=6.4 Hz, 2H), 5.07 (br s, 1H), 5.12 (s, 2H), 7.10 (d, J=8.3 Hz, 2H), 7.35 (m, 5H), 7.63 (d, J=8.3 Hz, 2H). m/z (APCI) 405 [C18H16NO2+H]+.

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