Benzaldehyde → alpha-Vinylbenzyl alcohol

온도

40 °C

To a DMF (0.3 mL) solution of Cu(O-Bu-t) (20 mg, 0.02 mmol) as synthesized according to the method described in the publication Inorg. Chim. Acta, 1981, 20, 2728, (R)-DTBM-SEGPHOS (35 mg, 0.03 mmol) and triethoxysilane fluoride (4.0 μL, 0.02 mmol), 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 40° C., and the mixture was stirred for 30 minutes. 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 as an (S)-form in a yield of 65% and an optical purity of 94% ee.

1. temperaturefor cooling to room temperature, to which
2. extractionthe mixture was extracted with ethyl acetate
3. washthe resulting organic layer was washed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. customAfter drying
6. distillationthe solvent was distilled off

ORD 기록

ord-3353b18e57c44e9185ae97fa46807060

출처 데이터셋

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07563916B2