| 92% |
In acetonitrile for 48h; Reflux; Darkness; Inert atmosphere; |
|
| 90% |
In acetonitrile for 24h; Reflux; |
|
| 82% |
for 0.0833333h; microwave irradiation; |
|
| 79% |
In acetonitrile at 70℃; for 184h; |
|
| 78% |
In acetonitrile at 82℃; for 48h; |
1.Y.1; 1.DN.1 Step 1 : (6-Hydroxyhexyl)triphenylphosphonium bromide
Step 1 : (6-Hydroxyhexyl)triphenylphosphonium bromide Chemical Formula: C24H28BrOP Molecular Weight: 443.36 [00644] 6-Bromo-l-hexanol (4.89 g, 27 mmol) and triphenylphosphine (7.87 g, 30 mmol) and 50 mL MeCN were combined in a round bottomed flask. The flask was fitted with a condenser and placed in a heating mantel and the reaction was allowed to stir at 82 °C for 48 h. After this time the reaction was allowed to cool to rt and the solution was cannulated into 200 mL Et^O, producing a white precipitate. The solids were allowed to settle and the solvent was decanted off. 20 mL DCM was added to dissolve the solids and then 100 mL Et^O was slowly added to afford a white precipitate. The solvent was then removed in vacuo to afford clean (6- hydroxyhexyl)triphenylphosphonium bromide (9.4 g, 21.2 mmol, for 78% yield). Ti-NMR (300 MHz, CDCI3) δ: ppm 7.80 (m, 15H); 3.80 (m, 2H); 3.65 (m, 2H); 2.23 (m, 2H); 1.68 (m, 4H); 1.52 (m, 4H). |
| 78% |
In acetonitrile at 82℃; for 48h; |
1.Y.1 Step 1 : (6-Hydroxyhexyl)triphenylphosphonium bromide
6-Bromo-l-hexanol (4.89 g, 27 mmol) and triphenylphosphine (7.87 g, 30 mmol) and 50 mL MeCN were combined in a round bottomed flask. The flask was fitted with a condenser and placed in a heating mantel and the reaction was allowed to stir at 82 °C for 48 h. After this time the reaction was allowed to cool to rt and the solution was cannulated into 200 mL Et20, producing a white precipitate. The solids were allowed to settle and the solvent was decanted off. 20 mL DCM was added to dissolve the solids and then 100 mL Et^O was slowly added to afford a white precipitate. The solvent was then removed in vacuo to afford clean (6- hydroxyhexyl)triphenylphosphonium bromide (9.4 g, 21.2 mmol, for 78% yield).1H NMR (300 MHz, CDCl3) δ: ppm 7.80 (m, 15H); 3.80 (m, 2H); 3.65 (m, 2H); 2.23 (m, 2H); 1.68 (m, 4H); 1.52 (m, 4H). |
| 30% |
In toluene for 6h; Reflux; |
|
|
In acetonitrile for 30h; Heating; |
|
|
In acetonitrile for 4h; Heating; |
|
|
In acetonitrile Heating / reflux; |
|
|
In acetonitrile for 72h; Heating / reflux; |
|
|
In acetonitrile for 48h; Reflux; |
9 (6-hydroxyhexyl)triphenylphosphonium bromide
(6-hydroxyhexyl)triphenylphosphonium bromide. A mixture of 6-hydroxyhexyl bromide (10.36 g, 0.057 mol) and triphenylphosphine (5 g, 0.019 mol) in 100 ml of acetonitrile was refluxed for 2 days. After removal of the solvent, the residue was washed three times with ether. The solid was purified by silica chromatography using heptane/ethyl acetate and methylene chloride/MeOH as eluent to give viscous pale white material. |
| 1.1 g |
In acetonitrile at 90℃; |
(6-Hydroxyhexyl)-triphenyl phosphonium bromide (8)
6-Bromo-1-hexanol (500 mg) and triphenylphosphine (800 mg) in MeCN (4 mL) were refluxed at 90 °C overnight. The reaction mixture was cooled to room temperature and concentrated. The resulting residue was dissolved in acetone and diluted with dry diethyl ether to precipitate the phosphonium salt. Afterstirring for 1 h, the supernatant was obtained by decantation anddried in vacuo to afford the desired phosphonium salt (8, 1.1 g) as white solids: [α]D24 -0.65 (c 0.97, CHCl3); 1H NMR (600 MHz, CDCl3) δ 1.43-1.77 (m, 8H), 2.03 (br s, 1H), 3.54-3.70 (m, 4H), 7.65-7.79 (m, 15H); 13C NMR (200 MHz, CDCl3) δ 22.0 (d, J=4.3 Hz), 22.2 (d, J=49.9 Hz), 24.5, 29.3 (d, J=15.9 Hz), 31.7, 61.0, 118.0 (d, J=86.0 Hz), 130.3 (d, J=12.3 Hz), 133.3 (d, J=10.1 Hz), 134.8 (d, J=2.2 Hz); HRFABMS calcd for C24H29OP [M+-Br] 363.1872, found: 363.1869. |
|
In acetonitrile |
|
|
In acetonitrile at 90℃; Inert atmosphere; |
|
| 0.95 mmol |
In acetonitrile for 48h; Reflux; Inert atmosphere; |
Synthesis of (6-hydroxyhexyl)triphenylphosphonium bromide(TPP)
To a stirred solution of 6-bromohexan-1-ol (5.0 g, 27.61 mmol) in 70 ml of acetonitrile at room temperature was added triphenylphosphine (7.967 g, 30.37 mmol), and the reaction mixture was heated under reflux for 48 h under a nitrogen atmosphere. Completion of the reaction was confirmed by thin layer chromatography (TLC). The solvent was evaporated under reduced pressure, the crude product was washed with ethanol (2 × 30 ml), and the solid was dried under high vacuum without further purification to afford the title compound (0.95 mmol) as a white solid. The product was confirmed by 1H NMR and liquid chromatography coupled to mass spectrometry (LC-MS). 1H NMR (400 MHz, CDCl3) δ 7.92-7.75 (m, 9H), 7.71 (td, J = 7.5, 3.4 Hz, 6H), 3.87-3.71 (m, 2H),3.63 (t, J = 5.4 Hz, 2H), 1.77-1.56 (m, 4H), 1.51 (d, J = 2.9 Hz, 4H). Mass spectrometry: m/z: calcd for [C24H28OP]+ ([M]+), 363.19; found, 363.16 (Supplementary Fig. 3a). |
| 0.95 mmol |
In acetonitrile for 48h; Inert atmosphere; Reflux; |
(6-hydroxyhexyl)triphenylphosphonium bromide (TPP) synthesis
To a stirred solution of 6-bromohexan-l-ol (5.0 g, 27.61 mmol) in 70 mL of acetonitrile at room temperature was added triphenylphosphine (7.967 g, 30.37 mmol) and the reaction mixture was refluxed for 48 h under a nitrogen atmosphere. Completion of the reaction was confirmed by thin layer chromatography (TLC). Then, the solvent was evaporated under reduced pressure, the crude product was washed with ethanol (2 x 30 mL), and the solid was dried under high vacuum without further purification to afford the title compound (0.95 mmol) as a white solid. The product was confirmed by NMR and LC MS. 1H MR (400 MHz, CDCb) d 7.92 - 7.75 (m, 9H), 7.71 (td, J = 7.5, 3.4 Hz, 6H), 3.87 - 3.71 (m, 2H), 3.63 (t, J = 5.4 Hz, 2H), 1.77 - 1.56 (m, 4H), 1.51 (d, J = 2.9 Hz, 4H). Mass m/z: calcd for [C24H2sOP]+ [M]+, 363.19; found, 363.16. |
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
