2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → 2,3-Dihydro-1,4-benzodioxin-6-methanol

Temperature

0 °C

2,3-Dihydro-benzo[1,4]dioxine-6-carbaldehyde [RN 29668-44-8] (3.04 g, 18.54 mmol) was dissolved in ethanol (100 mL) and cooled to 0° C. To the resulting solution was added sodium borohydride (1.41 g, 37.07 mmol). The resulting slurry was stirred at room temperature for 1 hour and then quenched with water (10 mL) before being concentrated to dryness under reduced pressure. The residue was partitioned between a 5% aqueous solution of sodium hydrogen carbonate (20 mL) and dichloromethane (2×50 mL). The organic phases were combined and dried over magnesium sulfate then evaporated under reduced pressure to provide and oil which was purified on silica gel using a dichloromethane and methanol solvent gradient. This provided the desired product as a colourless oil (3.00 g, 97%).

1. customquenched with water (10 mL)
2. concentrationbefore being concentrated to dryness under reduced pressure
3. customThe residue was partitioned between a 5% aqueous solution of sodium hydrogen carbonate (20 mL) and dichloromethane (2×50 mL)
4. dry with materialdried over magnesium sulfate
5. customthen evaporated under reduced pressure
6. customto provide
7. customoil which was purified on silica gel using a dichloromethane and methanol solvent gradient

ORD record

ord-4ba81d7b88114ecd95210bac8a4d532a

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141564B2