Reaktion #67403

Reaktionsgleichung

sodium hydroxide

2,2-difluoro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

lithium aluminum hydride

water

→

(2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol

Ausbeute 76.0%

Lösungsmittel

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was cooled to 0° C.
2. 2
   FiltrationThe resulting slurry was filtered
3. 3
   Waschenwashed with THF
4. 4
   SonstigeThe combined filtrate was evaporated to dryness
5. 5
   Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

Crude 2,2-difluoro-benzo[1,3]dioxole-5-carboxylic acid methyl ester (11.5 g) dissolved in 20 mL of anhydrous tetrahydrofuran (THF) was slowly added to a suspension of lithium aluminum hydride (4.10 g, 106 mmol) in anhydrous THF (100 mL) at 0° C. The mixture was then warmed to room temperature. After being stirred at room temperature for 1 hour, the reaction mixture was cooled to 0° C. and treated with water (4.1 g), followed by sodium hydroxide (10% aqueous solution, 4.1 mL). The resulting slurry was filtered and washed with THF. The combined filtrate was evaporated to dryness and the residue was purified by silica gel column chromatography to give (2,2-difluoro-benzo[1,3]dioxol-5-yl)-methanol (7.2 g, 76% over two steps) as a colorless oil.

Quelle