Sodium hydride → (3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanol

To a suspension of sodium hydride (a 60% oil suspension, 3.47 g, 86.8 mmol) in THF (150 mL) was added m-benzenedimethanol (10.00 g, 72.4 mmol) at room temperature, and stirred for 1 hour. To the resulting cloudy liquid was added t-butyldimethylchlorosilane (10.91 g, 72.4 mmol) at room temperature, and stirred for another 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with a 10% aqueous potassium hydrogensulfate solution and extracted three times with ethyl acetate. The ethyl acetate extract solution was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by a silica gel column chromatography (silica gel 400 mL; hexane/ethyl acetate=5/1 to 2/1) to obtain the title compound (9.25 g, 51%) as a colorless oil.

1. stirringstirred for another 4 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionthe residue was diluted with a 10% aqueous potassium hydrogensulfate solution
4. extractionextracted three times with ethyl acetate
5. extractionThe ethyl acetate extract solution
6. washwas washed with a saturated aqueous sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated
9. customThe residue was purified by a silica gel column chromatography (silica gel 400 mL; hexane/ethyl acetate=5/1 to 2/1)

ORD record

ord-a6c9747ea4b048f3be5d543930802ef3

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06787560B2