Reacción #6060

Ecuación de reacción

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

Lithium aluminum hydride

→

title compound

Rendimiento 41.2%

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

Rendimiento 41.2%

Disolventes

ether

ether

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction mixture was stirred at 0° C. for 0.5 h
2. 2
   OtroThe reaction was then quenched by the addition of 1.6 mL of water
3. 3
   FiltraciónThe reaction mixture was filtered
4. 4
   Lavadothe filter cake washed with diethyl ether
5. 5
   Concentraciónthe 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
   Otropurified on a 1.5×45 cm silica gel column
8. 8
   Lavadoeluted @ 2-3 psi with 200 mL of acetone:hexane (1:2 v/v)

Procedimiento

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).

Fuente