2-hex-5-enoxyoxane

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

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

Procedure: To a solution of 11.57 g of 6-(2-tetrahydropyranyloxy)-hex-1-ene in 200 ml of methylene chloride is added 10.8 g m-chloroperbenzoic acid and the mixture is stirred at room temperature for 18 h. The reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution followed by saturated sodium sulfite solution. The organic phase is dried, filtered and evaporated to give a clear oil which is purified by chromatography over silica gel using hexane/ether (4:1) as eluent to obtain 1,2-epoxy-6-(2-tetrahydropyranyloxy)-hexane; IR (CH2CH2): 1450, 1135, 1033 cm-1. The reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution The organic phase is dried filtered evaporated to give a clear oil which is purified by chromatography over silica gel

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

Procedure: To a solution of 8.5 g 5-hexen-1-ol in 100 ml tetrahydrofuran is added 14 ml dihydropyran followed by 0.5 g p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 18 h and then diluted with ether. The mixture is then washed with saturated aqueous sodium bicarbonate, dried, filtered and evaporated. The resulting oil is chromatographed over silica gel using hexane/ether (18:1) as eluent to give 6-(2-tetrahydropyranyloxy)hex-1-ene; NMR (CDCl3): delta 5.85 (m,1H), 4.6 (brs,1H). The mixture is then washed with saturated aqueous sodium bicarbonate dried filtered evaporated The resulting oil is chromatographed over silica gel

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

Procedure: To a solution of 8.5 g 5-hexen-1-ol in 100 ml tetrahydrofuran is added 14 ml dihydropyran followed by 0.5 g p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 18 h and then diluted with ether. The mixture is then washed with saturated aqueous sodium bicarbonate, dried, filtered and evaporated. The resulting oil is chromatographed over silica gel using hexane/ether (18:1) as eluent to give 6-(2-tetrahydropyranyloxy)hex-1-ene; NMR (CDCl3): delta 5.85 (m,1H), 4.6 (brs,1H). The mixture is then washed with saturated aqueous sodium bicarbonate dried filtered evaporated The resulting oil is chromatographed over silica gel

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

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

Procedure: To a solution of 11.57 g of 6-(2-tetrahydropyranyloxy)-hex-1-ene in 200 mL of methylene chloride is added 10.8 g m-chloroperbenzoic acid and the mixture is stirred at room temperature for 18 hours. The reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution followed by saturated sodium sulfite solution. The organic phase is dried, filtered and evaporated to give a clear oil which is purified by chromatography over silica gel using hexane/ether (4:1) as eluent to obtain 1,2-epoxy-6-(2-tetrahydropyranyloxy)-hexane; IR (CH2CH2): 1450, 1135, 1033 cm-1. The reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution The organic phase is dried filtered evaporated to give a clear oil which is purified by chromatography over silica gel

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

Procedure: To a solution of 8.5 g 5-hexen-1-ol in 100 mL tetrahydrofuran is added 14 mL dihydropyran followed by 0.5 g p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 18 hours and then diluted with ether. The mixture is then washed with saturated aqueous sodium bicarbonate, dried, filtered and evaporated. The resulting oil is chromatographed over silica gel using hexane/ether (18:1) as eluent to give 6-(2-tetrahydropyranyloxy)-hex-1-ene; NMR (CDCl3): delta 5.85 (m,1H), 4.6 (brs,1H). The mixture is then washed with saturated aqueous sodium bicarbonate dried filtered evaporated The resulting oil is chromatographed over silica gel

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

Procedure: To a solution of 11.57 g of 6-(2-tetrahydropyranyloxy)-hex-1-ene in 200 ml of methylene chloride is added 10.8 g m-chloroperbenzoic acid and the mixture is stirred at room temperature for 18 h. The reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution followed by saturated sodium sulfite solution. The organic phase is dried, filtered and evaporated to give a clear oil which is purified by chromatography over silica gel using hexane/ether (4:1) as eluent to obtain 1,2-epoxy-6-(2-tetrahydropyranyloxy)-hexane; IR (CH2CH2): 1450, 1135, 1033 cm-1. The reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution The organic phase is dried filtered evaporated to give a clear oil which is purified by chromatography over silica gel

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

Procedure: To a solution of 8.5 g 5-hexen-1-ol in 100 ml tetrahydrofuran is added 14 ml dihydropyran followed by 0.5 g p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 18 h and then diluted with ether. The mixture is then washed with saturated aqueous sodium bicarbonate, dried, filtered and evaporated. The resulting oil is chromatographed over silica gel using hexane/ether (18:1) as eluent to give 6-(2-tetrahydropyranyloxy)hex-1-ene; NMR (CDCl3): delta 5.85 (m,1H), 4.6 (brs,1H). The mixture is then washed with saturated aqueous sodium bicarbonate dried filtered evaporated The resulting oil is chromatographed over silica gel