3 Perylenepentanon
3-perylenepentanol, M4 39, 51
To a solution of 3-perylenepent-4-ynol, M3 (0.32 g, 0.957 mmol) in THF (20 mL), Pd/C (600 mg, 3 wt% on activated carbon) was added. Nitrogen gas was turned off, hydrogen gas balloons were used to supply H2 gas to the flask. The reaction mixture was stirred for 15 h under hydrogen atmosphere at room temperature. Ethyl acetate was added to the reaction mixture and the Pd/C was removed by filtration. Solvent was removed in vacuo to afford 3-perylenepentanol as yellow solid. Yield (0.43 g, 134 %). Rf 0.49 (hexane : ethyl acetate, 1 : 1). δH (500 MHz, CDCl3) 1.08 - 1.27 (2 H, m, 3’-CH2), 1.50 (3 H, br s, 2’-CH2) , 1.86 - 2.02 (2 H, m, 4’-CH2) , 2.66 (1 H, br t, J = 6.3 Hz, 1’-CH2) , 3.84 (1 H, br s, 5’-CH2OH), 7.07 …show more content…
The reaction mixture was refluxed at 78 °C for 2 h. The mixture was filtered and washed with methanol to give white solid (sodium 6-oxidonaphthalene-2-sulfonate). 1,4-bis(bromomethyl)benzene, M5 (4.54 g, 17.2 mmol) and sodium 6-oxidonaphalene-2-sulfonate (0.84 g, 3.13 mmol) were dissolved in 30 ml of DMSO. The mixture was stirred at room temperature overnight. The mixture was poured into ice cold acetone with continuous stirring. The mixture was filtered and washed with DCM and methanol to yield the title compound as pale yellow solid. Yield (0.13 g, 9 %). δH (400 MHz, DMSO-d6) 3.83 (2 H, s, CH2Br), 5.25 (2 H, s, CH2OAr), 7.25-7.26 (1 H, br d, J = 6.36 Hz, 3-ArH), 7.30-7.50 (2 H, m, 2’-ArH), 7.51-7.56 (1 H, m, 6-ArH), 7.58 (1 H, s, 4-ArH), 7.61-7.79 (3 H, m, 5,3’-ArH), 7.91 (1 H, d, J = 8.80 Hz, 2-ArH), 8.07 (1 H, s, 1-ArH). m/z (ES-) 223.0 (100%), 405.0 ([M - Na]-, …show more content…
Propargyl bromide (80 wt%. in toluene), M11 (0.45 ml, 4 mmol) was added into the reaction mixture and stirred at 100 °C for 2 hours. The reaction mixture was cooled to room temperature, added small amount of THF, and solvent was removed in vacuo. The white solid was washed with DCM to afford the title compound as white solid. Yield (0.55 g, 96 %). δH (300 MHz, CD3OD) 2.57 (1 H, br s, alkyne CH), 3.01 (1 H, br s, OCH2), 7.18 - 7.33 (1 H, m, 5-CH), 7.40 (1 H, br s, 1-CH), 7.85 (3 H, m, 6,7,8-CH), 8.29 (1 H, br s, 9-CH). vmax /cm-1 3290 (alkyne C-H stretch, m), 1234 (alkyl aryl ether C-O stretch, s) and 1185 (sulfonate S=O stretch,
To a solution of 3-perylenepent-4-ynol, M3 (0.32 g, 0.957 mmol) in THF (20 mL), Pd/C (600 mg, 3 wt% on activated carbon) was added. Nitrogen gas was turned off, hydrogen gas balloons were used to supply H2 gas to the flask. The reaction mixture was stirred for 15 h under hydrogen atmosphere at room temperature. Ethyl acetate was added to the reaction mixture and the Pd/C was removed by filtration. Solvent was removed in vacuo to afford 3-perylenepentanol as yellow solid. Yield (0.43 g, 134 %). Rf 0.49 (hexane : ethyl acetate, 1 : 1). δH (500 MHz, CDCl3) 1.08 - 1.27 (2 H, m, 3’-CH2), 1.50 (3 H, br s, 2’-CH2) , 1.86 - 2.02 (2 H, m, 4’-CH2) , 2.66 (1 H, br t, J = 6.3 Hz, 1’-CH2) , 3.84 (1 H, br s, 5’-CH2OH), 7.07 …show more content…
The reaction mixture was refluxed at 78 °C for 2 h. The mixture was filtered and washed with methanol to give white solid (sodium 6-oxidonaphthalene-2-sulfonate). 1,4-bis(bromomethyl)benzene, M5 (4.54 g, 17.2 mmol) and sodium 6-oxidonaphalene-2-sulfonate (0.84 g, 3.13 mmol) were dissolved in 30 ml of DMSO. The mixture was stirred at room temperature overnight. The mixture was poured into ice cold acetone with continuous stirring. The mixture was filtered and washed with DCM and methanol to yield the title compound as pale yellow solid. Yield (0.13 g, 9 %). δH (400 MHz, DMSO-d6) 3.83 (2 H, s, CH2Br), 5.25 (2 H, s, CH2OAr), 7.25-7.26 (1 H, br d, J = 6.36 Hz, 3-ArH), 7.30-7.50 (2 H, m, 2’-ArH), 7.51-7.56 (1 H, m, 6-ArH), 7.58 (1 H, s, 4-ArH), 7.61-7.79 (3 H, m, 5,3’-ArH), 7.91 (1 H, d, J = 8.80 Hz, 2-ArH), 8.07 (1 H, s, 1-ArH). m/z (ES-) 223.0 (100%), 405.0 ([M - Na]-, …show more content…
Propargyl bromide (80 wt%. in toluene), M11 (0.45 ml, 4 mmol) was added into the reaction mixture and stirred at 100 °C for 2 hours. The reaction mixture was cooled to room temperature, added small amount of THF, and solvent was removed in vacuo. The white solid was washed with DCM to afford the title compound as white solid. Yield (0.55 g, 96 %). δH (300 MHz, CD3OD) 2.57 (1 H, br s, alkyne CH), 3.01 (1 H, br s, OCH2), 7.18 - 7.33 (1 H, m, 5-CH), 7.40 (1 H, br s, 1-CH), 7.85 (3 H, m, 6,7,8-CH), 8.29 (1 H, br s, 9-CH). vmax /cm-1 3290 (alkyne C-H stretch, m), 1234 (alkyl aryl ether C-O stretch, s) and 1185 (sulfonate S=O stretch,