Reaktion #340484

Reaktionsgleichung

acetic acid

sodium borohydride

8-fluoro-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

→

(8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methanol

Ausbeute 95.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous mixture was extracted with ethyl acetate (80 ml)
2. 2
   WaschenThe organic phase was washed with water (30 ml), brine (30 ml)
3. 3
   Trocknendried over sodium sulfate
4. 4
   Einengenconcentrated under vacuum

Vorschrift

8-fluoro-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde (0.87 g: 4.8 mmol) was dissolved in ethanol (20 ml) and sodium borohydride (0.45 g; 11.95 mmol) was added at 0° C. The reaction mixture was stirred at rt for 2 h and poured into ice-water. The pH was adjusted to 5 by adding glacial acetic acid in portions and the aqueous mixture was extracted with ethyl acetate (80 ml). The organic phase was washed with water (30 ml), brine (30 ml), dried over sodium sulfate and concentrated under vacuum to give (8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methanol (0.84 g; 95% yield) as a yellow oil. 1H NMR (400 MHz, CD3OD) δ 6.66 (dd, 1H), 6.64 (br. s, 1H), 4.44 (s, 2H), 4.26 (s, 4H)

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