Ethyl Thioglycolate → HCID 89543486, Verbindung

HRID 922779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922779
[N+:1](/[CH:4]=[CH:5]/[CH:6]1[CH2:8][CH2:7]1)([O-:3])=[O:2].[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:10][SH:11]>C1COCC1>[CH:6]1([CH:5]([S:11][CH2:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][N+:1]([O-:3])=[O:2])[CH2:8][CH2:7]1

Komponenten

4

Edukt 2

HCID 12185Ethyl ThioglycolateHCID 14978083Cyclopropane, (2-nitroethenyl)-, (E)-

Produkt 1

HCID 89543486HCID 89543486, VerbindungAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(E)-(2-Nitrovinyl)cyclopropane (4-11, 750 mg, 6.63 mmol) was taken up in THF (20 mL). To this was added ethyl thioglycolate (0.88 mL, 7.98 mmol) then TEA (1.2 mL, 8.61 mmol) at rt. After stirring overnight the mixture was concentrated. The crude product was subjected to silica gel chromatography (40 g, 0-20% EtOAc/hexanes, 10 minute gradient) to afford ethyl 2-((1-cyclopropyl-2-nitroethyl)thio)acetate (4-12, 1.46 g, 94%) as a clear oil. 1H NMR (399 MHz, CDCl3): δ 4.73-4.58 (m, 2H); 4.21 (q, J=7.1 Hz, 2H); 3.34 (d, J=6.2 Hz, 2H); 2.93 (dt, J=9.9, 7.2 Hz, 1H); 1.30 (t, J=7.1 Hz, 3H); 1.00-0.90 (m, 1H); 0.69 (dd, J=8.0, 1.6 Hz, 2H); 0.47-0.36 (m, 2H).

Aufarbeitung

  1. customat rt
  2. concentrationwas concentrated
  3. customwas subjected to silica gel chromatography (40 g, 0-20% EtOAc/hexanes, 10 minute gradient)

Quellen und Nachweise

ORD-Eintrag
ord-e7652e7abd3d4b5c8cccbcda51d4bdbf
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278960B2

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