Ammonia → 5-(2',2'-Dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol

HRID 1196174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196174
N.Cl[C:3]1(Cl)[C:5]([CH3:7])([CH3:6])[CH:4]1[CH2:8][CH2:9][C:10]([CH3:14])([OH:13])[C:11]#[CH:12].[Na]>CCOCC>[CH3:6][C:5]1([CH3:7])[CH2:3][CH:4]1[CH2:8][CH2:9][C:10]([CH3:14])([OH:13])[C:11]#[CH:12]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 5360545SodiumHCID 543866045-(2',2'-Dichloro-3'3'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol

Produkt 1

HCID 541287215-(2',2'-Dimethylcyclopropyl)-3-methyl-1-pentyn-3-olAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Ammonia, 1 l, is placed in a reaction flask. A solution of 150 g (0.63 mol) of 5-(2',2'-dichloro-3',3'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol dissolved in 750 ml of ether is added dropwise. Sodium (62 g, 2.7 mol) in small portions is added at -30° to -35° within 21/2 hours until the blue coloration persists. The ammonia is evaporated and 1.5 liters of hexane are added dropwise followed by the addition of 100 ml of ethanol. The reaction mixture is poured into a mixture of 150 ml of acetic acid in 500 g of ice, washed neutral in succession with water, saturated sodium carbonate solution, saturated sodium chloride solution, dried and evaporated. The crude product (100.2 g) is distilled. In this manner there are obtained 90.5 g (85%) of 5-(2',2'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol.

Aufarbeitung

  1. additionis added dropwise
  2. customThe ammonia is evaporated
  3. addition1.5 liters of hexane are added dropwise
  4. additionfollowed by the addition of 100 ml of ethanol
  5. additionThe reaction mixture is poured into a mixture of 150 ml of acetic acid in 500 g of ice
  6. washwashed neutral in succession with water, saturated sodium carbonate solution, saturated sodium chloride solution
  7. customdried
  8. customevaporated
  9. distillationThe crude product (100.2 g) is distilled

Quellen und Nachweise

ORD-Eintrag
ord-a5a87f93ece047d697dfd375887ad7da
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05113021

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