Sulfuric acid magnesium salt (1:1) → (4-Propylphenyl)methanol

Temperature

0 °C

Under argon condition, tert-butyldimethyl((4-propylbenzyl)oxy)-silane (275 mg, 1.04 mmol) was dissolved in 5 mL of dry THF, and then n-butylammonium fluoride (TBAF; 1.56 mL, 1.0 M solution in tetrahydrofuran, 1.56 mmol) were slowly added thereto, and the mixture was stirred for 30 minutes at 0° C. Upon completion of the reaction, the reaction was terminated by adding 5 mL of aqueous saturated ammonium chloride solution. The reaction mixture was extracted with ethyl acetate (5 mL×4) and the organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure and purified by column chromatography to obtain 198 mg (0.838 mmol, 95%) of the desired compound.

1. customUpon completion of the reaction
2. customthe reaction was terminated
3. additionby adding 5 mL of aqueous saturated ammonium chloride solution
4. extractionThe reaction mixture was extracted with ethyl acetate (5 mL×4)
5. customthe organic layer thus obtained
6. customto remove water
7. filtrationThe precipitate was filtered out
8. concentrationthe resulting solution was concentrated by distillation under reduced pressure
9. custompurified by column chromatography

ORD record

ord-9838e242d024453fae557506f3ecd01c

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809012B2