Pyridine → 1-(3,5-Bis(methoxycarbonyl)phenyl)-2-(1-adamantyl)ethyne

HRID 1994659

Reaktionsgleichung

Reaktionsgleichung von HRID 1994659
Br[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:16]([C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)#[CH:17].C(N(CC)CC)C.N1C=CC=CC=1>[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:10][O:9][C:7]([C:6]1[CH:11]=[C:2]([C:17]#[C:16][C:18]23[CH2:27][CH:22]4[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]4)[CH2:19]2)[CH2:25]3)[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=1)=[O:8]

Komponenten

8

Edukt 4

HCID 1049PyridineHCID 8471TriethylamineHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 5947811-Ethynyladamantane

Produkt 1

HCID 675073001-(3,5-Bis(methoxycarbonyl)phenyl)-2-(1-adamantyl)ethyneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

In a 1 L four-neck flask provided with a thermometer, a Dimroth condenser, a nitrogen inlet pipe and an agitator, 125 g of dimethyl 5-bromoisophthalate (0.458 mol), 1.1 g of triphenyl phosphine (0.00419 mol), 0.275 g of copper iodide (0.00144 mol) and 64.26 g of the obtained 1-ethynyladamantane (0.401 mol) were charged and nitrogen was passed into the flask. Then, 375 mL of dehydrated triethylamine and 200 mL of dehydrated pyridine were added therein and the mixture was agitated and dissolved. After nitrogen was passed into the flask for one hour, 0.3 g of dichlorobis (triphenyl phosphine) palladium (0.000427 mol) was quickly added and the mixture was heated and refluxed in an oil bath. Then, triethylamine and pyridine was removed under reduced pressure to obtain a brown viscous solution. The solution was added to 500 mL of water and filtered to separate a solid. The solid was washed with 500 mL of water, 500 mL of 5 mol/L hydrochloric acid and 500 mL of water each two times and dried under pressure at 50° C., thus obtaining 121.5 g of 1-(3,5-bis(methoxycarbonyl)phenyl)-2-(1-adamantyl)ethyne (the yield was 86%).

Aufarbeitung

  1. customIn a 1 L four-neck flask provided with a thermometer
  2. dissolutiondissolved
  3. temperaturethe mixture was heated
  4. temperaturerefluxed in an oil bath
  5. customThen, triethylamine and pyridine was removed under reduced pressure
  6. customto obtain a brown viscous solution
  7. filtrationfiltered
  8. customto separate a solid
  9. washThe solid was washed with 500 mL of water, 500 mL of 5 mol/L hydrochloric acid and 500 mL of water each two times
  10. customdried under pressure at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-9b4587bf556b4bfcabe47e7ea5566218
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652125B2

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