(Dimethyl sulfide)trihydroboron → (4-((1,3-Dioxolan-2-yl)methyl)phenyl)methanol

Temperature

0 °C

To a cooled (0° C.) solution of 4-((1,3-dioxolan-2-yl)methyl)benzoic acid (1.02 g, 4.92 mmol) in anhydrous THF (63.5 mL), a solution of borane dimethylsulfide complex (2.0 M in THF, 12.29 mL, 24.59 mmol) was added dropwise. The reaction mixture was stirred at this temperature for 5 minutes and then the coolant removed. The reaction mixture was stirred at RT for 16 hours. The reaction mixture was cooled to 0° C. and methanol (1 mL) was added. The reaction mixture was diluted with water and saturated aqueous sodium hydrogen carbonate and then extracted with ethyl acetate (×2). The combined organic extracts were washed with brine, dried (magnesium sulphate) filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-50% ethyl acetate in iso-hexane to afford the title compound (0.936 g, 98%).

1. customthe coolant removed
2. stirringThe reaction mixture was stirred at RT for 16 hours
3. additionmethanol (1 mL) was added
4. additionThe reaction mixture was diluted with water and saturated aqueous sodium hydrogen carbonate
5. extractionextracted with ethyl acetate (×2)
6. washThe combined organic extracts were washed with brine
7. dry with materialdried (magnesium sulphate)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe crude material was purified by silica gel chromatography
11. washeluting with 0-50% ethyl acetate in iso-hexane

ORD record

ord-d2d32735a12a4d058ca7cb3a56c18653

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877774B2