Reaktion #543768

Reaktionsgleichung

benzo[1,3]dioxol-5-yl-acetic acid

methanol

→

oil

Ausbeute 84.4%

2-Benzo[1,3]dioxol-5-yl-ethanol

Ausbeute 84.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(CAUTION—exothermic reaction)
2. 2
   workup.ADDITIONwas added
3. 3
   workup.WAITAfter 0.5 hour at room temperature
4. 4
   Sonstigethe mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
5. 5
   ExtraktionThe organic extract
6. 6
   Sonstigewas dried
7. 7
   Sonstigeevaporated

Vorschrift

A solution of benzo[1,3]dioxol-5-yl-acetic acid (2.5 g, 13.9 mmol) in tetrahydrofuran (15 ml) under argon at −10° C. was treated dropwise with borane-dimethylsulfide complex (1.45 ml, 15.3 mmol). The mixture was stirred at ambient temperature for 1.5 hours (CAUTION—exothermic reaction). The orange solution was cooled to ˜5° C. (ice bath) and methanol (1.4 ml) was added. After 0.5 hour at room temperature, the mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic extract was dried and evaporated to give a yellow oil (1.95 g, 84%).

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