Chlorotrimethylsilane → 3-(Trimethylsilyl)benzenemethanol

To a solution of 3-bromobenzylalcohol (9.35 g, 50 mmol) in diethyl ether (50 ml) at 0° C. was added dropwise 1.5M butyllithium (66.7 ml) and the mixture was stirred 30 min. Then trimethylsilylchloride (11.39 g, 105 mmol) in diethyl ether (50 ml) was added dropwise and the mixture was stirred at room temperature 18 hours. The reaction mixture was treated with ice water (100 ml) and the organic layer extracted, washed with water, brine, dried over MgSO4 and concentrated. The crude product was dissolved in 90% aqueous methanol (100 ml) and refluxed 1 hour. The solvents were removed and 3-trimethylsilylbenzylalcohol was purified by distillation.

1. stirringthe mixture was stirred at room temperature 18 hours
2. extractionthe organic layer extracted
3. washwashed with water, brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. dissolutionThe crude product was dissolved in 90% aqueous methanol (100 ml)
7. temperaturerefluxed 1 hour
8. customThe solvents were removed
9. distillation3-trimethylsilylbenzylalcohol was purified by distillation

ORD record

ord-dc0edb14b0fe487489c4fc76b3432e11

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05693668