Pempidine → Butyl 3-phenylprop-2-ynoate

HRID 1859275

Reaktionsgleichung

Reaktionsgleichung von HRID 1859275
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN1C(C)(C)CCCC1(C)C.[C:31]1([C:37]#[CH:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl[C:40]([O:42][CH2:43][CH2:44][CH2:45][CH3:46])=[O:41]>CN(C)C1C=CN=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[C:31]1([C:37]#[C:38][C:40]([O:42][CH2:43][CH2:44][CH2:45][CH3:46])=[O:41])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

8

Edukt 4

HCID 6603PempidineHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 61140Butyl chloroformate

Produkt 1

HCID 11769566Butyl 3-phenylprop-2-ynoateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.25 g (1.1 mmol) of palladium(II) acetate and 1.16 g (4.4 mmol) of triphenylphosphine are introduced into 100 ml of dichloromethane in a 250 ml round-bottomed flask under argon. The yellow solution is stirred at room temperature for 1 h. Then 0.06 g (0.5 mmol) of 4-dimethylaminopyridine, 8.53 g (55.5 mmol) of 1,2,2,6,6-pentamethylpiperidine and 5.1 g (50 mmol) of phenylacetylene are added. The mixture is heated to reflux at 40° C. and then 6.83 g (50 mmol) of n-butyl chloroformate are added dropwise over the course of 1 h. After a reaction time of 20 h, the reaction mixture is worked up by distillation to isolate n-butyl phenylpropynoate in 85% yield.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureto reflux at 40° C.
  3. distillationAfter a reaction time of 20 h, the reaction mixture is worked up by distillation

Quellen und Nachweise

ORD-Eintrag
ord-e4cf8245303548ff8d5fa6461efaaf0c
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06153786

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