Реакция #46178

Уравнение реакции

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

Выход 76.0%

Растворители

tetrahydrofuran

THF

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was cooled to 0° C.
2. 2
   ФильтрацияThe resulting slurry was filtered
3. 3
   Промывкаwashed with THF
4. 4
   ДругоеThe combined filtrate was evaporated to dryness
5. 5
   Другоеthe residue was purified by silica gel column chromatography

Методика

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.

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