1-iododecane

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

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

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

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

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-Iododecane (1.21 g) was added to a stirred mixture of 3-azabicyclo[3.1.0]hexane-2,4 dione (0.5 g), potassium carbonate (0.62 g) and tetrabutylammonium bromide (1.45 g) in dichloromethane (50 ml) at room temperature and the resulting mixture was stirred for 24 hours. The mixture was filtered and the filtrate was then washed with water (2×100 ml), dried (MgSO4) and evaporated in vacuo to give a brown oil. The oil was purified by column chromatography on silica gel (100 g) using hexane as eluant. Combination and evaporation of the appropriate fractions gave the title compound as a colourless oil. The mixture was filtered the filtrate was then washed with water (2×100 ml) dried (MgSO4) evaporated in vacuo to give a brown oil The oil was purified by column chromatography on silica gel (100 g) Combination and evaporation of the appropriate fractions

Conditions: temp:63.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 3,5-diphenyl-4[(2-methoxyethoxy)methoxy]-phenol (0.946 g, 2.7 mmol) in DMF (15 ml) was added K2CO3 (0.746 g, 5.4 mmol) and iododecane (1.632 g, 5.4 mmol). The reaction mixture was warmed to ˜63° C. After ˜20 h, additional K2CO3 (0.373 g, 2.7 mmol) and iododecane (0.816 g, 2.7 mmol) were added. Heating was continued for an additional 20 h followed by stirring at room temperature for ˜20 h. The reaction mixture was concentrated in vac and the residue taken up in EtOAc (50 ml) and water (20 ml). The layers were shaken and separated and the organic layer was washed with water (3×10 ml), brine (2×10 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (hexane and 5% EtOAc/Hex) to give the product as a brown oil (0.897 g, 68%); 1H NMR (400 MHz, DMSO-d6) δ0.83-0.88 (m, 3H), 1.20-1.37 (m, 12H), 1.37-1.46 (m, 2H), 1.68-1.76 (m, 2H), 2.71-2.75 (m, 2H), 2.86-2.88 (m, 2H), 3.01 (s, 3H), 4.03 (t, J=6.4 Hz, 2H), 4.22 (s, 2H), 6.87 (s, 2H), 7.34-7.39 (m, 2H), 7.42-7.48 (m, 4H), 7.56-7.60 (m, 4H); IR (film) 2940, 1590, 1460, 1190 cm−1; mass spectrum [(+)ESI], m/z 508 (M+NH4)−. Heating was continued for an additional 20 h The reaction mixture was concentrated in vac The layers were shaken separated the organic layer was washed with water (3×10 ml), brine (2×10 ml) dried over Na2SO4 filtered the filtrate concentrated in vac dried The residue was purified by flash chromatography (hexane and 5% EtOAc/Hex)

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

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

Procedure: To a suspension of sodium hydride (80% in oil, 3.2 g, 104 mmol) in 100 ml of THF, there is slowly added a solution of 2-(1-adamantyl)-4-bromophenol (29 g, 95 mmol) in 200 ml of THF. The mixture is stirred until the evolution of gas ceases at which point 27.8 g (23 ml, 104 mmol) of 1-iododecane and 100 ml of DMF are added. The mixture it stirred for 12 hours at ambient temperature, poured into water, extracted with ether, dried and the solvents evaporated. The resulting residue is purified by passage through a silica column (eluant: heptane), yielding 40.7 g (96%) of 2(1-adamantyl)-4-bromo-1-decyloxybenzene. Melting point: 69°-70° C. are added extracted with ether dried the solvents evaporated The resulting residue is purified by passage through a silica column (eluant: heptane)

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

Procedure: To a suspension of sodium hydride (80% in oil, 3.2 g, 104 mmol) in 100 ml of THF, there is slowly added a solution of 2-(1-adamantyl)-4-bromophenol (29 g, 95 mmol) in 200 ml of THF. The mixture is stirred until the evolution of gas ceases at which point 27.8 g (23 ml, 104 mmol) of 1-iododecane and 100 ml of DMF are added. The mixture it stirred for 12 hours at ambient temperature, poured into water, extracted with ether, dried and the solvents evaporated. The resulting residue is purified by passage through a silica column (eluant: heptane), yielding 40.7 g (96%) of 2(1-adamantyl)-4-bromo-1-decyloxybenzene. Melting point: 69°-70° C. are added extracted with ether dried the solvents evaporated The resulting residue is purified by passage through a silica column (eluant: heptane)

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

Procedure: To a suspension of sodium hydride (80% in oil, 3.2 g, 104 mmol) in 100 ml of THF, there is slowly added a solution of 2-(1-adamantyl)-4-bromophenol (29 g, 95 mmol) in 200 ml of THF. The mixture is stirred until the evolution of gas ceases at which point 27.8 g (23 ml, 104 mmol) of 1-iododecane and 100 ml of DMF are added. The mixture is stirred for 12 hours at ambient temperature, poured into water, extracted with ether, dried and the solvents evaporated. The resulting residue is purified by passage through a silica column (eluant: heptane), yielding 40.7 g (96%) of 2-(1-adamantyl)-4-bromo-1-decyloxybenzene. Melting point: 69°-70° C. are added extracted with ether dried the solvents evaporated The resulting residue is purified by passage through a silica column (eluant: heptane)