Реакция #6060

Уравнение реакции

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

Lithium aluminum hydride

→

title compound

Выход 41.2%

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

Выход 41.2%

Растворители

ether

ether

diethyl ether

Условия реакции

Обработка

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

Методика

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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