1-BENZOFURAN-2-YLMETHANOL

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:

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

Procedure: 36.40 g (139 mmol) of triphenylphosphine are added, all at once and with vigorous stirring, to a solution, cooled to 0° C., of 10.40 g (70 mmol) of 2-hydroxymethyl-benzo[b]furan and 46 g (139 mol) of CBr4 in 220 ml of ether. After stirring for 4 hours at 20° C., the precipitate formed is suctioned off and washed with Et2O; the filtrate is dried and concentrated, and the residue is then chromatographed on silica, eluting with a mixture of cyclohexane/CH2Cl2 =80/20, to yield the expected compound in the form of an oil. the precipitate formed washed with Et2O the filtrate is dried concentrated the residue is then chromatographed on silica eluting with a mixture of cyclohexane/CH2Cl2 =80/20

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: Thionyl chloride (5.14 mL, 70.46 mmol) was added dropwise to a solution of benzofuran-2-methanol (3.58 g, 23.48 mmol) and pyridine (10 drops) in dichloromethane (60 mL). Stirring was continued at room temperature for 18 hours. The mixture was carefully diluted with water and extracted with methylene chloride. The organic extracts were washed with aqueous sodium bicarbonate, dried (MgSO4) and concentrated to afford crude product which was purified by flash column chromatography (10% ethyl acetate/hexanes) to afford 2.77 g (69%) of pure product as a yellow oil. extracted with methylene chloride The organic extracts were washed with aqueous sodium bicarbonate dried (MgSO4) concentrated to afford crude product which was purified by flash column chromatography (10% ethyl acetate/hexanes)