2-(oxan-2-yloxy)acetonitrile

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

Procedure: A solution of 35 g of tetrahydropyran-2-yloxy acetonitrile in 100 ml of ether is added dropwise to a slurry of 10 g of lithium aluminum hydride in 300 ml of ether and 100 ml of tetrahydrofuran. The slurry is refluxed for 210 minutes, cooled, and 25 ml of saturated potassium carbonate solution is added at a rate that maintains gentle reflux. After 90 minutes the slurry is filtered and the solid is washed with ether. The filtrate is evaporated in vacuo and distilled to give 33.6 g of 2-(tetrahydropyran-2-yloxy)-ethylamine, boiling point 41.5° - 46°C at 0.5-0.8 mm. The slurry is refluxed for 210 minutes cooled After 90 minutes the slurry is filtered the solid is washed with ether The filtrate is evaporated in vacuo distilled

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

Procedure: A solution of 35 g of tetrahydropyran-2-yloxy acetonitrile in 100 ml of ether is added dropwise to a slurry of 10 g of lithium aluminum hydride in 300 ml of ether and 100 ml of tetrahydrofuran. The slurry is refluxed for 210 minutes, cooled, and 25 ml of sat. potassium carbonate solution is added at a rate that maintains gentle reflux. After 90 minutes the slurry is filtered and the solid is washed with ether. The filtrate is evaporated in vacuo and distilled to give 33.6 g of 2-(tetrahydropyran-2-yloxy)ethylamine, boiling point 41.5°-46°C at 0.5-0.8 mm. The slurry is refluxed for 210 minutes cooled After 90 minutes the slurry is filtered the solid is washed with ether The filtrate is evaporated in vacuo distilled

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

Procedure: A solution of 35 g of tetrahydropyran-2-yloxy acetonitrile in 100 ml of ether is added dropwise to a slurry of 10 g of lithium aluminum hydride in 300 ml of ether and 100 ml of tetrahydrofuran. The slurry is refluxed for 210 minutes, cooled, and 25 ml of sat. potassium carbonate solution is added at a rate that maintains gentle reflux. After 90 minutes the slurry is filtered and the solid is washed with ether. The filtrate is evaporated in vacuo and distilled to give 33.6 g of 2-(tetrahydropyran-2-yloxy)ethylamine, boiling point 41.5°-46°C at 0.5-0.8 mm. The slurry is refluxed for 210 minutes cooled After 90 minutes the slurry is filtered the solid is washed with ether The filtrate is evaporated in vacuo distilled

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

Procedure: To a solution of tetrahydropyran-2-yloxyethanonitrile (6.0 g, 42.49 mmol) in ethanol (15 ml) was added aqueous sodium hydroxide solution (10M, 15 ml). Following the initial exothermic reaction the solution was heated under reflux for 1.5 hours, diluted with ethanol (30 ml) and the pH adjusted to 8 by the addition of carbon dioxide pellets. The resulting gelatinous suspension was diluted with acetonitrile (60 ml), filtered at 60° C. through diatomaceous earth and the insoluble material extracted in a similar manner with a mixture of acetonitrile/ethanol/water (4:3:1, 2×120 ml). The crude product was purified by dissolution in warm isopropanol, filtration at 0° C. through diatomaceous earth, evaporation of the solvent in vacuo and trituration of the residue with acetone at 0° C. to yield sodium tetrahydropyran-2-yloxyethanoate (6.24 g, 34.26 mmol) as a colorless powder, m.p. 198°-205° C.; exothermic reaction the solution was heated under reflux for 1.5 hours filtered at 60° C. through diatomaceous earth the insoluble material extracted in a similar manner with a mixture of acetonitrile/ethanol/water (4:3:1, 2×120 ml) The crude product was purified by dissolution in warm isopropanol filtration at 0° C. through diatomaceous earth, evaporation of the solvent in vacuo and trituration of the residue with acetone at 0° C.

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

Procedure: To a solution of tetrahydropyran-2-yloxyethanonitrile (6.0 g, 42.49 mmol) in ethanol (15 ml) was added aqueous sodium hydroxide solution (10M, 15 ml). Following the initial exothermic reaction the solution was heated under reflux for 1.5 hours, diluted with ethanol (30 ml) and the pH adjusted to 8 by the addition of carbon dioxide pellets. The resulting gelatinous suspension was diluted with acetonitrile (60 ml), filtered at 60° C. through diatomaceous earth and the insoluble material extracted in a similar manner with a mixture of acetonitrile/ethanol/water (4:3:1, 2×120 ml). The crude product was purified by dissolution in warm isopropanol, filtration at 0° C. through diatomaceous earth, evaporation of the solvent in vacuo and trituration of the residue with acetone at 0° C. to yield sodium tetrahydropyran-2-yloxyethanoate (6.24 g, 34.26 mmol) as a colorless powder, m.p. 198°-205° C.; exothermic reaction the solution was heated under reflux for 1.5 hours filtered at 60° C. through diatomaceous earth the insoluble material extracted in a similar manner with a mixture of acetonitrile/ethanol/water (4:3:1, 2×120 ml) The crude product was purified by dissolution in warm isopropanol filtration at 0° C. through diatomaceous earth, evaporation of the solvent in vacuo and trituration of the residue with acetone at 0° C.

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

Procedure: A solution of 35 g of tetrahydropyran-2-yloxy acetonitrile in 100 ml of ether is added dropwise to a slurry of 10 g of lithium aluminum hydride in 300 ml of ether and 100 ml of tetrahydrofuran. The slurry is refluxed for 210 minutes, cooled, and 25 ml of saturated potassium carbonate solution is added at a rate that maintains gentle reflux. After 90 minutes the slurry is filtered and the solid is washed with ether. The filtrate is evaporated in vacuo and distilled to give 33.6 g of 2-(tetrahydropyran-2-yloxy)-ethylamine, boiling point 41.5° - 46°C at 0.5-0.8 mm. The slurry is refluxed for 210 minutes cooled After 90 minutes the slurry is filtered the solid is washed with ether The filtrate is evaporated in vacuo distilled

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

Procedure: A solution of 35 g of tetrahydropyran-2-yloxy acetonitrile in 100 ml of ether is added dropwise to a slurry of 10 g of lithium aluminum hydride in 300 ml of ether and 100 ml of tetrahydrofuran. The slurry is refluxed for 210 minutes, cooled, and 25 ml of sat. potassium carbonate solution is added at a rate that maintains gentle reflux. After 90 minutes the slurry is filtered and the solid is washed with ether. The filtrate is evaporated in vacuo and distilled to give 33.6 g of 2-(tetrahydropyran-2-yloxy)ethylamine, boiling point 41.5°-46°C at 0.5-0.8 mm. The slurry is refluxed for 210 minutes cooled After 90 minutes the slurry is filtered the solid is washed with ether The filtrate is evaporated in vacuo distilled

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

Procedure: To a solution of tetrahydropyran-2-yloxyethanonitrile (6.0 g, 42.49 mmol) in ethanol (15 ml) was added aqueous sodium hydroxide solution (10M, 15 ml). Following the initial exothermic reaction the solution was heated under reflux for 1.5 hours, diluted with ethanol (30 ml) and the pH adjusted to 8 by the addition of carbon dioxide pellets. The resulting gelatinous suspension was diluted with acetonitrile (60 ml), filtered at 60° C. through diatomaceous earth and the insoluble material extracted in a similar manner with a mixture of acetonitrile/ethanol/water (4:3:1, 2×120 ml). The crude product was purified by dissolution in warm isopropanol, filtration at 0° C. through diatomaceous earth, evaporation of the solvent in vacuo and trituration of the residue with acetone at 0° C. to yield sodium tetrahydropyran-2-yloxyethanoate (6.24 g, 34.26 mmol) as a colorless powder, m.p. 198°-205° C.; exothermic reaction the solution was heated under reflux for 1.5 hours filtered at 60° C. through diatomaceous earth the insoluble material extracted in a similar manner with a mixture of acetonitrile/ethanol/water (4:3:1, 2×120 ml) The crude product was purified by dissolution in warm isopropanol filtration at 0° C. through diatomaceous earth, evaporation of the solvent in vacuo and trituration of the residue with acetone at 0° C.