4-(oxan-2-yloxy)but-2-yn-1-ol

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

Procedure: An oven dried 500 ml RBF was charged with NaH (60% in mineral oil) (1.41 g, 35.3 mmol) and suspended in DMF (100 mL). The mixture was cooled to 0° C. and 4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol (prepared in accordance with the procedures of Tamaru et al., Bull. Chem. Soc. Jpn., 1995, 1689-1705) (6.0 g, 35.3 mmol) was added. The reaction mixture was allowed to reach room temperature and stirred for one hour. To the mixture was added iodoethane (20.8 g, 133 mmol). The reaction mixture was stirred for 3.5 hours at room temperature before being quenched with ice/H2O and extracted with MeOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (1-20% MeOAc/hexane) provided 4.71 g of 2-(4-ethoxy-but-2-ynyloxy)-tetrahydro-pyran as a clear oil. An oven dried 500 ml RBF , 1995, 1689-1705) (6.0 g, 35.3 mmol) was added to reach room temperature The reaction mixture was stirred for 3.5 hours at room temperature before being quenched with ice/H2O extracted with MeOAc The organic phase was washed with brine dried (Na2SO4) concentrated

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

Procedure: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. was added dropwise was evaporated the residue was poured into 200 ml of water The aqueous solution was extracted with hexane (2×100 ml) re-extracted with ether (3×100 ml) The combined ether extracts were washed with 100 ml of brine dried over magnesium sulfate evaporated

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

Procedure: To a solution of 90 g (1.07 mol) of 2-butyne-1,4-diol and 9 g of p-toluenesulfonic acid in 1000 ml of tetrahydrofuran, cooled to 0° C., there were added dropwise 104.88 ml (96.69 g, 1.15 mol) of dihydropyran, and thereafter the reaction mixture was stirred for 3 hours at room temperature. It was then neutralized with triethylamine and evaporated in vacuo. The residue was purified by silica gel column chromatography (2000 g) using hexane-ethyl acetate (80:20) as eluant, to yield 2-butyne-1,4-diol monotetrahydropyranyl ether and a small amount of the bis-tetrahydropuranyl ether. evaporated in vacuo The residue was purified by silica gel column chromatography (2000 g)

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

Procedure: To a solution of 90 g (1.07 mol) of 2-butyne-1,4-diol and 9 g of p-toluenesulfonic acid in 1000 ml of tetrahydrofuran, cooled to 0° C., there were added dropwise 104.88 ml (96.69 g, 1.15 mol) of dihydropyran, and thereafter the reaction mixture was stirred for 3 hours at room temperature. It was then neutralized with triethylamine and evaporated in vacuo. The residue was purified by silica gel column chromatography (2000 g) using hexane-ethyl acetate (80:20) as eluant, to yield 2-butyne-1,4-diol monotetrahydropyranyl ether and a small amount of the bis-tetrahydropuranyl ether. evaporated in vacuo The residue was purified by silica gel column chromatography (2000 g)

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

Procedure: An oven dried 500 ml RBF was charged with NaH (60% in mineral oil) (1.41 g, 35.3 mmol) and suspended in DMF (100 mL). The mixture was cooled to 0° C. and 4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol (prepared in accordance with the procedures of Tamaru et al., Bull. Chem. Soc. Jpn., 1995, 1689-1705) (6.0 g, 35.3 mmol) was added. The reaction mixture was allowed to reach room temperature and stirred for one hour. To the mixture was added iodoethane (20.8 g, 133 mmol). The reaction mixture was stirred for 3.5 hours at room temperature before being quenched with ice/H2O and extracted with MeOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (1-20% MeOAc/hexane) provided 4.71 g of 2-(4-ethoxy-but-2-ynyloxy)-tetrahydro-pyran as a clear oil. An oven dried 500 ml RBF , 1995, 1689-1705) (6.0 g, 35.3 mmol) was added to reach room temperature The reaction mixture was stirred for 3.5 hours at room temperature before being quenched with ice/H2O extracted with MeOAc The organic phase was washed with brine dried (Na2SO4) concentrated

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

Procedure: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. was added dropwise was evaporated the residue was poured into 200 ml of water The aqueous solution was extracted with hexane (2×100 ml) re-extracted with ether (3×100 ml) The combined ether extracts were washed with 100 ml of brine dried over magnesium sulfate evaporated

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

Procedure: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic add and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. of p-toluenesulfonic add was evaporated the residue was poured into 200 ml of water The aqueous solution was extracted with hexane (2×100 ml) re-extracted with ether (3×100 ml) The combined ether extracts were washed with 100 ml of brine dried over magnesium sulfate evaporated

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

Procedure: To a mixture of 5.0 g of 2-butyne-l,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. was added dropwise was evaporated the residue was poured into 200 ml of water The aqueous solution was extracted with hexane (2×100 ml) re-extracted with ether (3×100 ml) The combined ether extracts were washed with 100 ml of brine dried over magnesium sulfate evaporated

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

Procedure: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. was added dropwise was evaporated the residue was poured into 200 ml of water The aqueous solution was extracted with hexane (2×100 ml) re-extracted with ether (3×100 ml) The combined ether extracts were washed with 100 ml of brine dried over magnesium sulfate evaporated

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

Procedure: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic add and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. of p-toluenesulfonic add was evaporated the residue was poured into 200 ml of water The aqueous solution was extracted with hexane (2×100 ml) re-extracted with ether (3×100 ml) The combined ether extracts were washed with 100 ml of brine dried over magnesium sulfate evaporated

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

Procedure: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. was added dropwise was evaporated the residue was poured into 200 ml of water The aqueous solution was extracted with hexane (2×100 ml) re-extracted with ether (3×100 ml) The combined ether extracts were washed with 100 ml of brine dried over magnesium sulfate evaporated

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

Procedure: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic add and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. of p-toluenesulfonic add was evaporated the residue was poured into 200 ml of water The aqueous solution was extracted with hexane (2×100 ml) re-extracted with ether (3×100 ml) The combined ether extracts were washed with 100 ml of brine dried over magnesium sulfate evaporated