반응 #46178

반응 방정식

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

수율 76.0%

용매

tetrahydrofuran

THF

반응 조건

후처리

1. 1
   온도the reaction mixture was cooled to 0° C.
2. 2
   여과The resulting slurry was filtered
3. 3
   세척washed with THF
4. 4
   기타The combined filtrate was evaporated to dryness
5. 5
   기타the residue was purified by silica gel column chromatography

실험 절차

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, 38 mmol, 76% over two steps) as a colorless oil.

출처