Acetylene → N-Butyl propiolate

HRID 1859276

Reaktionsgleichung

Reaktionsgleichung von HRID 1859276
CN1C(C)(C)CC[CH2:4][C:3]1(C)C.C#C.Cl[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16]>CN(C)C1C=CN=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClCCl>[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:16])[C:3]#[CH:4]

Komponenten

7

Edukt 3

HCID 6326Acetylene3×HCID 6603PempidineHCID 61140Butyl chloroformate

Produkt 1

HCID 11366990N-Butyl propiolateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

0.42 g (0.36 mmol) of tetrakis(triphenylphosphine)palladium(0), 20 mg (0.16 mmol) of 4-dimethylamino-pyridine and 2.87 g (18.5 mmol) of 1,2,2,6,6-penta-methylpiperidine are introduced into 30 ml of dichloromethane in a 60 ml autoclave under argon. Then 10 bar of acetylene are injected, and the autoclave is heated to 40° C. 5 g (36.6 mmol) of n-butyl chloroformate are pumped in over the course of 10 min, and then acetylene is further injected to 20 bar. The amount of acetylene taken up is replenished hourly over the course of 24 h, and, after cooling, the reaction discharge is flushed with nitrogen and the reaction mixture is distilled. n-Butyl propiolate is isolated in 85% yield.

Aufarbeitung

  1. customare pumped in over the course of 10 min
  2. customtaken up is replenished hourly over the course of 24 h
  3. temperatureafter cooling
  4. customthe reaction discharge is flushed with nitrogen
  5. distillationthe reaction mixture is distilled

Quellen und Nachweise

ORD-Eintrag
ord-22efaec56935488392cb6fff9daf2f20
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06153786

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