Reaktion #1964258

Reaktionsgleichung

water

hydrochloric acid

2-methyl-5-phenylfuran-3-carbaldehyde

bromo(1,4-dioxaspiro[4.5]dec-8-yl)magnesium tetrahydrofuran

→

title compound

Ausbeute 91.0%

1,4-dioxaspiro[4.5]dec-8-yl(2-methyl-5-phenylfuran-3-yl)methanol

Ausbeute 91.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONafter the completion of the dropwise addition
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with saturated brine
4. 4
   Trocknendried over magnesium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe residue was purified by silica gel column (0% ethyl acetate/hexane to 30% ethyl acetate/hexane)

Vorschrift

To a solution of 2-methyl-5-phenylfuran-3-carbaldehyde (2.4 g) in tetrahydrofuran (30 mL) was added dropwise 0.4N bromo(1,4-dioxaspiro[4.5]dec-8-yl)magnesium-tetrahydrofuran solution (33.5 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 1 hr. The reaction mixture was treated with 1N hydrochloric acid, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (0% ethyl acetate/hexane to 30% ethyl acetate/hexane) to give the title compound (3.9 g, 91%) as a yellow crystal.

Quelle