1-(chloromethyl)-2,3,4,5,6-pentamethylbenzene

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

Procedure: A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,3,4,5,6-pentamethylbenzyl chloride (309 mg, 1.57 mmol) in abs. EtOH (2 mL) is heated at 95° C. for 24 h. The reaction mixture is cooled to RT, evaporated to dryness, and the residue suspended in Et2O. The insoluble material is filtered to give 186 mg of the product 234. 1H NMR (DMSO-d6) δ 11.20 (s, 2 H), 7.25-6.95 (m, 10 H), 5.85 (s, 2 H), 4.84 (s, 2 H), 2.38 (s, 6 H), 2.20 (s, 9 H); MS: m/z 415 (M++1). evaporated to dryness The insoluble material is filtered

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

Procedure: A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,3,4,5,6-pentamethylbenzyl chloride (309 mg, 1.57 mmol) in abs. EtOH (2 mL) is heated at 95° C. for 24 h. The reaction mixture is cooled to RT, evaporated to dryness, and the residue suspended in Et2O. The insoluble material is filtered to give 186 mg of the product 234. 1H NMR (DMSO-d6) δ 11.20 (s, 2 H), 7.25-6.95 (m, 10 H), 5.85 (s, 2 H), 4.84 (s, 2 H), 2.38 (s, 6 H), 2.20 (s, 9 H); MS: m/z 415 (M++1). evaporated to dryness The insoluble material is filtered

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

Procedure: A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,3,4,5,6-pentamethylbenzyl chloride (309 mg, 1.57 mmol) in abs. EtOH (2 mL) is heated at 95° C. for 24 h. The reaction mixture is cooled to RT, evaporated to dryness, and the residue suspended in Et2O. The insoluble material is filtered to give 186 mg of the product 234. 1H NMR (DMSO-d6) δ 11.20 (s, 2H), 7.25-6.95 (m, 10H), 5.85 (s, 2H), 4.84 (s, 2H), 2.38 (s, 6H), 2.20 (s, 9H); MS: m/z 415 (M++1). evaporated to dryness The insoluble material is filtered

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 250 ml roundbottom flask equipped with a condenser, stirrer, thermometer and dropping funnel with nitrogen inlet was charged with 100 ml THF in which pentamethylbenzyl chloride (19.8 g, 0.10 mol) was dissolved. The solution was cooled to -20° C. and sodium cyclopentadienyl (60 ml, 2.0 M in THF) was added; the solution was stirred for 48 hours at 22° C. GC analysis showed 90% conversion to pentamethylcyclopentadienyl. A precipitate was filtered off and the solvent was evaporated. The remaining residue was recrystallized from hot dichloromethane/petroleum ether. After recrystallization, pentamethylcyclopentadiene (16 g) was obtained. The product was characterized by GC, GC-MS, 13C and 1H NMR. A 250 ml roundbottom flask equipped with a condenser, stirrer was dissolved A precipitate was filtered off the solvent was evaporated The remaining residue was recrystallized from hot dichloromethane/petroleum ether After recrystallization

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

Procedure: Synthesized according to General Procedure A: 2,3,4,5,6-pentamethylbenzyl chloride (4{14}, 5 g, 25.4 mmol, 1 equiv.), piperazine (13.1 g, 152.5 mmol, 6 equiv.), THF (55.5 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{14} (5.31 g, 85%) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 3.52 (s, 2H), 2.80 (t, 4H, J=4.8 Hz), 2.45 (br s, 4H), 2.32 (s, 6H), 2.25 (s, 3H), 2.23 (s, 6H), 1.63 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 133.9, 133.7, 132.3, 131.9, 57.2, 54.1, 46.5, 17.0, 16.8, 16.6. Synthesized Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{14} (5.31 g, 85%) as a white solid

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

Procedure: A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,3,4,5,6-pentamethylbenzyl chloride (309 mg, 1.57 mmol) in abs. EtOH (2 mL) is heated at 95° C. for 24 h. The reaction mixture is cooled to RT, evaporated to dryness, and the residue suspended in Et2O. The insoluble material is filtered to give 186 mg of the product 234. 1H NMR (DMSO-d6) δ 11.20 (s, 2 H), 7.25-6.95 (m, 10 H), 5.85 (s, 2 H), 4.84 (s, 2 H), 2.38 (s, 6 H), 2.20 (s, 9 H); MS: m/z 415 (M++1). evaporated to dryness The insoluble material is filtered