Tetrabutylammonium Fluoride → 4-Hydroxy-2-methylbenzofuran

A solution of the crude 4-t-butyldimethylsilyloxy-2-methylbenzofuran (1.822 g, 6.99 mmol) in THF (28 mL) and cooled to 0° C. (ice water bath) was treated with TBAF (14 mL, 13.00 mmol, 1.0 M in THF). After 30 min. the solution was concentrated under reduced pressure and diluted with 150 mL of Et2O and 300 mL of H2O in a separatory funnel. The mixture was shaken and separated in a separatory funnel. The aqueous layer was extracted with Et2O (2×125 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was passed through a column of silica gel [5 to 20% EtOAc/hexanes] and concentrated under reduced pressure to give the product as a white solid (0.9923 g. 96%). A portion (0.052 g) of the material was purified by silica gel chromatography [5 to 20% EtOAc/hexanes] to give the product as a white solid (0.0382 g, 73% recovery). C9H8O2.0.3H2O

1. concentrationAfter 30 min. the solution was concentrated under reduced pressure
2. additiondiluted with 150 mL of Et2O and 300 mL of H2O in a separatory funnel
3. customseparated in a separatory funnel
4. extractionThe aqueous layer was extracted with Et2O (2×125 mL)
5. dry with materialThe combined organic layers were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. concentrationconcentrated under reduced pressure

ORD record

ord-3511274f576a47b195c7d565f8df395f

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06844344B2