2-(2-phenylphenyl)ethanol

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: A mixture of the alcohol prepared above (8.5 g, 43 mmol), 2-bromoethyltetrahydro-2-pyranylether (17.9 g, 86 mmol) and potassium hydroxide (9.6 g, 171 mmol) in dimethylsulfoxide (100 ml) was stirred at ambient temperature for 72 h. An extra batch of 2-bromoethyltetrahydro-2-pyranylether (3.6 g, 17 mmol) was added and the mixture stirred for 48 h at ambient temperature. Water (350 ml) was added and the mixture was extracted with diethylether (2×250 ml). The organic phases were combined, washed with water (100 ml), dried (MgSO4) and concentrated in vacuo. The residue was submitted to column chromatography on silica gel (400 ml) using heptane and ethyl acetate (3:2) as eluent to give 6.6 g of 2-(2-(biphenyl-2-yl)ethoxy)ethanol as an oil. the mixture stirred for 48 h at ambient temperature the mixture was extracted with diethylether (2×250 ml) washed with water (100 ml) dried (MgSO4) concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Bromobiphenyl (20.0 g, 86 mmol) in THF (85 ml) was dropwise added to a refluxing suspension of magnesium (2.1 g, 86 mmol) in THF (15 ml). The reaction mixture was refluxed for 18 h and an extra batch of 2-bromobiphenyl (2.0 g, 8.6 mmol) was added. The reaction mixture was refluxed for 2 h and cooled to 0° C. on an icebath. Ethyleneoxide (14.0 g, 0.32 mol) was was added. The reaction mixture was refluxed for 18 h, cooled to 0° C. and a saturated solution of ammonium chloride (100 ml) was dropwise added at this temperature. The reaction mixture was diluted with diethyl ether (100 ml) and concentrated hydrochloric acid was added until pH 2. The organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was submitted to column chromatography on silica gel (800 ml) using heptane and ethyl acetate (7:3) as eluent to give 8.5 g of 2-(biphenyl-2-yl)ethanol as an oil. The reaction mixture was refluxed for 18 h The reaction mixture was refluxed for 2 h The reaction mixture was refluxed for 18 h cooled to 0° C. was added until pH 2 The organic phase was separated dried (MgSO4) concentrated in vacuo

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

Procedure: 2-biphenyl ethanol (1 g, 5 mmol), 4-nitrophenol (834 mg, 6 mmol), and triphenylphosphine (1.59 g, 6 mmol) was dissolved in 20 mL dichloromethane. The solution was chilled in an ice-water bath prior to the addition of diethylazodicarboxylate (949 μl, 6 mmol). The reaction was then stirred overnight, and the ice-water bath slowly warmed to room temperature. Crude product was purified by flash chromatography to yield 640 mg crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ 8.1 (d), 7.6 (m), 7.47–7.41 (m), 7.34 (m), 7.17 (m), 4.39 (t, 2H), 3.13 (t, 2H). The solution was chilled in an ice-water bath Crude product was purified by flash chromatography