Reaktion #2289442

Reaktionsgleichung

ethyl trans-2-((tert-butyldiphenylsilyloxy)methyl)cyclopropanecarboxylate

water

sodium hydroxide

water

LAH

→

trans-(2-((tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol

Ausbeute 74.5%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe precipitate was removed by filtration
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   SonstigeThe obtained residue was purified by silica gel column chromatography (solvent gradient; 1→30% ethyl acetate/hexane)

Vorschrift

To a suspension of LAH (0.92 g, 24.24 mmol) in THF (100 mL) was added a solution of ethyl trans-2-((tert-butyldiphenylsilyloxy)methyl)cyclopropanecarboxylate (21.4 g, 55.94 mmol) in THF (20 mL) at 0° C., and the mixture was stirred for 2 hr. To the reaction mixture were added successively water (0.92 mL), 15% aqueous sodium hydroxide solution (0.92 mL) and water (2.76 mL). The precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 1→30% ethyl acetate/hexane) to give trans-(2-((tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol (14.16 g, 41.66 mmol, 74%) as a colorless oil.

Quelle