Benzaldehyde → alpha-Vinylbenzyl alcohol

온도

60 °C

To a DMF (0.2 mL) solution of CuF.3PPh3.2EtOH (10 mg, 0.01 mmol) as synthesized according to the method described in the foregoing publication and dppf (8 mg, 0.014 mmol) (this catalyst preparation method is designated as “A”; hereinafter the same), benzaldehyde (0.020 mL, 0.20 mmol) and vinyltrimethoxysilane (62 μL, 0.40 mmol) were added at room temperature under an argon atmosphere, the temperature was then raised to 60° C., and the mixture was stirred for 3 hours. Thereafter, the reaction mixture was allowed to stand for cooling to room temperature, to which was then added tetrabutylammonium fluoride (TBAF) (1M/THF, 0.5 mL), and the mixture was stirred for 10 minutes. After adding water, the mixture was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After drying, the solvent was distilled off, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane: 1/9 to 1/4), thereby obtaining desired 1-phenyl-2-propen-1-ol in a yield of 100%.

1. custom3PPh3.2EtOH (10 mg, 0.01 mmol) as synthesized
2. customthis catalyst preparation method
3. temperaturefor cooling to room temperature, to which
4. extractionthe mixture was extracted with ethyl acetate
5. washthe resulting organic layer was washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customAfter drying
8. distillationthe solvent was distilled off

ORD 기록

ord-2267b6e46bd944d09f0bfeb09e8cd56d

출처 데이터셋

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07563916B2