1,1-Bis(propan-2-yl) 3,3-dimethoxycyclobutane-1,1-dicarboxylate → 1,1-Bis(propan-2-yl) 3-oxocyclobutane-1,1-dicarboxylate

HRID 1966158

Reaktionsgleichung

Reaktionsgleichung von HRID 1966158
C[O:2][C:3]1(OC)[CH2:6][C:5]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])([C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[CH2:4]1>FC(F)(F)C(O)=O.O.CCOC(C)=O>[O:2]=[C:3]1[CH2:6][C:5]([C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])([C:13]([O:15][CH:16]([CH3:17])[CH3:18])=[O:14])[CH2:4]1

Komponenten

4

Edukt 1

HCID 49133591,1-Bis(propan-2-yl) 3,3-dimethoxycyclobutane-1,1-dicarboxylate

Produkt 1

HCID 49133571,1-Bis(propan-2-yl) 3-oxocyclobutane-1,1-dicarboxylateAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 22392675Trifluoroacetic acid waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate (3 g, 0.01 mol) in 20 mL of trifluoroacetic acid-water (95:5) was stirred at 0° C. for 4 h. The reaction was diluted with EtOAc, washed with water, saturated NaHCO3 solution, and brine, dried over MgSO4 and evaporated to give crude product (2.4 g) as yellow oil, which was used directly in the next step. H NMR (CDCl3, 400 MHz) δ 5.07 (2H, h, J=6.8 Hz), 3.54 (4H, s), 1.23 (12H, d, J=6.8 Hz) ppm.

Aufarbeitung

  1. washwashed with water, saturated NaHCO3 solution, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2a13090c981f4d908f0a8ebc045a16ec
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420629B2

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