1-methylfluoren-9-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). the reaction mixture was refluxed for 24 h extracted with Et2O (4×125 ml) The combined organic layers were washed with brine (2×125 ml) dried over MgSO4 filtered the volatiles removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: from phenylmagnesium chloride and 1-methyl-9-fluorenone;

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.32 g (6.2 mmol) of 3'-methyl-2-biphenylcarboxylic acid, 40 mL of CH2Cl2 and 0.70 mL (9.6 mmol) of SOCl2 was warmed to reflux for 2 h. The solution was cooled to room temperature and 1.10 mL (9.4 mmol) of SnCl4 was added dropwise with stirring. The dark brown homogenous mixture was stirred for 18 h, poured into 50 mL of cold saturated aqueous NaHCO3, and extracted with 2×50 mL of ether. The ether extracts were combined and washed with 30 mL of saturated NaHCO3 solution, 30 mL of H2 0 and 30 mL of brine, dried (MgSO4) and concentrated in vacuo. Chromatography over SiO2 (Biotage 40 S) using 1% EtOAc in hexanes provided 168 mg (16% yield) of 1-methyl-9-fluorenone (Ladd, D. L. et al., Synthesis and dopaminergic binding of 2-aryldopamine analogues: Phenethylamines, 3-benzazepines, and 9-(aminomethyl)fluorenes. J. Med. Chem. 1986, 29, 1904-1912). was warmed to reflux for 2 h The dark brown homogenous mixture was stirred for 18 h extracted with 2×50 mL of ether washed with 30 mL of saturated NaHCO3 solution, 30 mL of H2 0 and 30 mL of brine dried (MgSO4) concentrated in vacuo