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

HRID 1453325

Reaktionsgleichung

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

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). 1H NMR (CDCl3) δ: 1.54-1.87 (m, 8H), 1.94 (t, J=2.65 Hz, 1H), 2.45 (dt, J1=7.33 Hz, J2=2.78 Hz, 2H), 2.71 (t, J=7.58 Hz, 2H), 2.87 (p, J=7.96 Hz, 1H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-ecd306e68e784c28a0020e8697147fcf
Quelldatensatz: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07473790B2

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