反应详情

1-Methylfluoren-9-one (46) was prepared according to Mortier et al. (D. Tilly, S. S. Samanta, A.-S. Castanet, A. De, J. Mortier, Eur. J. Org. Chem. 2005, 174). 1-Methylfluoren-9-one (46) was reduced according to the general procedure of Carruthers et al. (W. Carruthers, D. Whitmarsh, J. Chem. Soc. Perkin Trans, I 1973, 1511). 1-Methylfluoren-9-one (46) (6.8 g, 35 mmol) was dissolved in 450 ml propionic acid. Red phosphorus (7.4 g) and 100 ml concentrated HI were added and the reaction mixture was refluxed for 24 h. Quantitative conversion was shown by TLC. The reaction mixture was diluted with 500 ml water, neutralized with NaOH and extracted with Et2O (4×125 ml). The combined organic layers were washed with brine (2×125 ml), dried over MgSO4, filtered and the volatiles removed in vacuo to afford 6.1 g (97%) 47 as a white solid. The analytical data were consistent with the literature (G. L. Grunewald, A. E. Carter, D. J. Sall, J. A. Monn, J. Med. Chem. 1988, 31, 60 and M. J. Shapiro, J. Org. Chem. 1978, 43, 3769).

1. temperaturethe reaction mixture was refluxed for 24 h
2. extractionextracted with Et2O (4×125 ml)
3. washThe combined organic layers were washed with brine (2×125 ml)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customthe volatiles removed in vacuo