Hydrochloric Acid → 1-Cyclopentyl-pent-4-yn-1-one

HRID 858868

Reaktionsgleichung

Reaktionsgleichung von HRID 858868
N1C=CC=CC=1S[C:8](=[O:13])[CH2:9][CH2:10][C:11]#[CH:12].[CH:14]1([Mg]Br)[CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>C1COCC1>[CH:14]1([C:8](=[O:13])[CH2:9][CH2:10][C:11]#[CH:12])[CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 58762612Pent-4-ynethioic acid S-pyridin-2-yl EsterHCID 178419650HCID 178419650, Verbindung

Produkt 1

HCID 224997991-Cyclopentyl-pent-4-yn-1-oneAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of pent-4-ynethioic acid S-pyridin-2-yl ester (17.9 g, 94 mmol), dissolved in THF (900 mL) cooled to −78° C. was added cyclopentylmagnesium bromide (2.0 M, 94 mL, 188.5 mmol). The reaction was stirred for 15 minutes, and then warmed to −50° C. The reaction was poured into 500 mL 1 N HCl and the layers were separated. The aqueous layer was extracted with 2×200 mL diethyl ether and the organic layers were combined. The organics were then washed with 300 mL of 1 N NaOH. The organic layer was dried over Mg SO4, and the solids were removed by filtration. The solvent was removed by rotary evaporation to give the desired compound (14.0 g, 99% yield).

Aufarbeitung

  1. temperaturewarmed to −50° C
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with 2×200 mL diethyl ether
  4. washThe organics were then washed with 300 mL of 1 N NaOH
  5. dry with materialThe organic layer was dried over Mg SO4
  6. customthe solids were removed by filtration
  7. customThe solvent was removed by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-f920eae2f20c4242a34a21514f08dce6
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148226B2

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