5-phenylpent-4-yn-1-ol

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 solution of 5-phenylpent-4-yn-1-ol (250 mg) in dry CH2Cl2 (2 ml) was added to a suspension of pyridinium chlorochromate (520 mg) in dry CH2Cl2 (3 ml). The mixture was stirred for 2.5 hours and diluted with ether, and the organic solution was decanted off. The oily residue was treated with ether (5×20 ml) and the extracts were washed successively with 5% NaHCO3, water and brine. After drying, the solvent was removed to yield 5-phenylpent-4-ynal. the organic solution was decanted off The oily residue was treated with ether (5×20 ml) the extracts were washed successively with 5% NaHCO3, water and brine After drying the solvent was removed

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

Procedure: A mixture of 1-phenyl-5-tetrahydropyranyloxypent-1-yne (0.2 g), absolute ethanol (4 ml) and p-toluenesulphonic acid (20 mg) was stirred at room temperature for 3 hours. The reaction mixture was diluted with water (40 ml) and extracted with ether (2×20 ml). The ether extracts were washed with saturated NaHCO3 solution, dried over MgSO4 and purified by chromatography on silica (20 g), eluting with 10% ether in hexane grading to 100% ether, followed by 10% ethyl acetate in ether. The solvent was removed to give 5-phenylpent-4-yn-1-ol as a colourless oil. extracted with ether (2×20 ml) The ether extracts were washed with saturated NaHCO3 solution dried over MgSO4 purified by chromatography on silica (20 g) eluting with 10% ether in hexane grading to 100% ether The solvent was removed

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

Procedure: A solution of 5-phenylpent-4-yn-1-ol (250 mg) in dry CH2Cl2 (2 ml) was added to a suspension of pyridinium chlorochromate (520 mg) in dry CH2Cl2 (3 ml). The mixture was stirred for 2.5 hours and diluted with ether, and the organic solution was decanted off. The oily residue was treated with ether (5×20 ml) and the extracts were washed successively with 5% NaHCO3, water and brine. After drying, the solvent was removed to yield 5-phenylpent-4-ynal. the organic solution was decanted off The oily residue was treated with ether (5×20 ml) the extracts were washed successively with 5% NaHCO3, water and brine After drying the solvent was removed

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

Procedure: A mixture of 1-phenyl-5-tetrahydropyranyloxypent-1-yne (0.2 g), absolute ethanol (4 ml) and p-toluenesulphonic acid (20 mg) was stirred at room temperature for 3 hours. The reaction mixture was diluted with water (40 ml) and extracted with ether (2×20 ml). The ether extracts were washed with saturated NaHCO3 solution, dried over MgSO4 and purified by chromatography on silica (20 g), eluting with 10% ether in hexane grading to 100% ether, followed by 10% ether acetate in ether. The solvent was removed to give 5-phenylpent-4-yn-1-ol as a colourless oil. extracted with ether (2×20 ml) The ether extracts were washed with saturated NaHCO3 solution dried over MgSO4 purified by chromatography on silica (20 g) eluting with 10% ether in hexane grading to 100% ether The solvent was removed