Reaktion #6060

Reaktionsgleichung

Diisopropyl 3,3-dimethoxy-cyclobutane-1,1-dicarboxylate

Lithium aluminum hydride

→

title compound

Ausbeute 41.2%

3.3-Bis(hydroxymethyl)-1,1-dimethoxycyclobutane

Ausbeute 41.2%

Lösungsmittel

ether

ether

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at 0° C. for 0.5 h
2. 2
   SonstigeThe reaction was then quenched by the addition of 1.6 mL of water
3. 3
   FiltrationThe reaction mixture was filtered
4. 4
   Waschenthe filter cake washed with diethyl ether
5. 5
   Einengenthe combine ether filtrates were concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue (3.0 g) was dissolved in 2 mL of methylene chloride
7. 7
   Sonstigepurified on a 1.5×45 cm silica gel column
8. 8
   Wascheneluted @ 2-3 psi with 200 mL of acetone:hexane (1:2 v/v)

Vorschrift

Diisopropyl 3,3-dimethoxy-cyclobutane-1,1-dicarboxylate (6.0 g, 20.8 mmol), prepared as described by P. E. Pigou and C. H. Schiesser, J Org Chem, 53, 3841-3 (1988), was dissolved in 200 mL of anhydrous diethyl ether and the ether solution was cooled to 0° C. with stirring under a nitrogen atmosphere. Lithium aluminum hydride (1.6 g, 42 mmol) was added to the ether solution in portions and the reaction mixture was stirred at 0° C. for 0.5 h. The reaction was then quenched by the addition of 1.6 mL of water, followed by 1.6 mL of 15% aqueous sodium hydroxide solution and 4.8 mL of water. The reaction mixture was filtered, the filter cake washed with diethyl ether and the combine ether filtrates were concentrated under reduced pressure. The residue (3.0 g) was dissolved in 2 mL of methylene chloride and purified on a 1.5×45 cm silica gel column eluted @ 2-3 psi with 200 mL of acetone:hexane (1:2 v/v), followed by 200 mL of acetone:hexane (1:1 v/v) to give 1.51 g (41% yield) of the title compound; MS DCI/NH3M-Z: 194 (M+NH4)+ ; 1H NMR (CDCl3) δ 1.99 (s, 4H), 2.35 (t, 2H-OH), 3.16 (s, 6H), 3.77 (d, 4H).

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