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Pyridine → Diethyl 2-(3-(butoxysulfonyl)cyclobutylidene)malonate

HRID 1259402
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259402
C(Cl)(Cl)(Cl)Cl.O=[C:7]1[CH2:10][CH:9]([S:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:13])=[O:12])[CH2:8]1.[C:19]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].N1C=CC=CC=1>C1COCC1.CCCCCC.Cl[Ti](Cl)(Cl)Cl.C(OCC)(=O)C>[CH2:15]([O:14][S:11]([CH:9]1[CH2:10][C:7](=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]([O:27][CH2:28][CH3:29])=[O:26])[CH2:8]1)(=[O:13])=[O:12])[CH2:16][CH2:17][CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 1049PyridineHCID 5943Carbon TetrachlorideHCID 7761Diethyl MalonateHCID 58380588Butyl 3-oxocyclobutane-1-sulfonate

Produkt 1

HCID 58380583Diethyl 2-(3-(butoxysulfonyl)cyclobutylidene)malonateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24193
Titanium Tetrachloride
Katalysator
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8058HexaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

TiCl4 (0.5 mL, 4.854 mmol) was added to a solution of THF (25 mL) and CCl4 (5 mL) at 0° C. This was followed by the addition of butyl 3-oxocyclobutane-1-sulfonate (0.5 g, 2.42 mmol) at 0° C. and diethyl malonate (0.38 mL, 2.42 mmol). The resulting mixture was stirred at 0° C. for 5 minutes. Then pyridine (0.78 mL, 9.68 mmol) in THF (10 mL) was added and stirred at room temperature for 96 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with sodium bicarbonate solution, brine solution, dried over anhydrous Na2SO4 and concentrated. Purification by column chromatography on silica gel (13% ethyl acetate in hexane) afforded 200 mg of the product (25% yield).

Aufarbeitung

  1. stirringstirred at room temperature for 96 hours
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with sodium bicarbonate solution, brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (13% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-35642db176f84c3186343b7bb016eb80
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466289B2

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