反应详情

温度

0 °C

A solution of (3-hydroxy-2-methylphenyl)(phenyl)methanone prepared as in Step 2 (1.60 g, 7.54 mmole) in anhydrous CH2Cl2 (70 mL) was cooled to 0° C. Triethylsilane (32.5 mL, 203 mmole) and TFA (52.3 mL, 679 mmole) were added in portions at 0° C. over a period of 3 days with the mixture brought back to reflux after each addition. After 3 days, the mixture was cooled, poured into sat. NH4Cl (200 mL) and extracted with CH2Cl2 (3×200 mL). The combined extracts were washed with H2O (200 mL), brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The crude product was purified by silica chromatography (95:5 hexanes:EtOAc) to give 1.19 g (80% yield) of the product as a pale yellow oil: EIHRMS m/z 198.1072 (M+, C14H14O, Calc'd 198.1045).

1. temperatureto reflux
2. additionafter each addition
3. temperaturethe mixture was cooled
4. extractionextracted with CH2Cl2 (3×200 mL)
5. washThe combined extracts were washed with H2O (200 mL), brine (100 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a yellow oil
10. customThe crude product was purified by silica chromatography (95:5 hexanes:EtOAc)