2-(oxan-2-yl)ethanol

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

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

Procedure: 2-(Tetrahydro-2H-pyran-2-yl)ethanol (465 mg) was dissolved in dry DCM (10 mL) and triethylamine (996 mg) was added. The stirred solution was cooled in an ice bath under nitrogen and methanesulphonyl chloride (359 mg) was added dropwise over 5 mins. The reaction was allowed to warm to room temperature as the ice bath melted and was left for 16 h. The mixture was then shaken with saturated sodium bicarbonate solution and the aqueous layer was extracted with DCM (×2). The combined organic extracts were washed with brine, dried using a hydrophobic frit and evaporated to give the title compound as a brown oil (718 mg). The stirred solution was cooled in an ice bath under nitrogen the aqueous layer was extracted with DCM (×2) The combined organic extracts were washed with brine dried evaporated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of tetrahydro-2H-pyran-2-ylacetaldehyde (528 mg) in ethanol (5 mL) was added sodium borohydride granules (156 mg). The mixture was heated at 50° C. for 2 h under nitrogen. After cooling, the solvent was evaporated and the residue treated with brine. The mixture was acidified by careful addition of 2N HCl and this mixture was extracted with DCM (×3). The combined organics were washed with brine, dried using a hydrophobic frit and evaporated to give the title compound as a clear oil (465 mg). After cooling the solvent was evaporated the residue treated with brine The mixture was acidified by careful addition of 2N HCl this mixture was extracted with DCM (×3) The combined organics were washed with brine dried evaporated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of tetrahydro-2H-pyran-2-ylacetaldehyde (528 mg) in ethanol (5 mL) was added sodium borohydride granules (156 mg). The mixture was heated at 50° C. for 2 h under nitrogen. After cooling, the solvent was evaporated and the residue treated with brine. The mixture was acidified by careful addition of 2N HCl and this mixture was extracted with DCM (×3). The combined organics were washed with brine, dried using a hydrophobic frit and evaporated to give the title compound as a clear oil (465 mg). After cooling the solvent was evaporated the residue treated with brine The mixture was acidified by careful addition of 2N HCl this mixture was extracted with DCM (×3) The combined organics were washed with brine dried evaporated

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 2-(tetrahydro-pyran-2-yl)-ethanol (53.5 g, 0.41 mol) in dichloromethane (1 L) was added pyridinium chlorochromate (176.8 g, 0.82 mol) in small portions at room temperature. The dark suspension was stirred for 3 h. The mixture was filtered through a short pad of silica gel. The filtrate was concentrated in vacuo and the residue was diluted with n-hexane (400 mL). The mixture was filtered through a short pad of silica gel and the filtrate was concentrated in vacuo to afford (tetrahydro-pyran-2-yl)-acetaldehyde (38 g) as a colorless oil. The mixture was filtered through a short pad of silica gel The filtrate was concentrated in vacuo the residue was diluted with n-hexane (400 mL) The mixture was filtered through a short pad of silica gel the filtrate was concentrated in vacuo

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

Procedure: To a solution of (tetrahydro-pyran-2-yl)-acetic acid ethyl ester (77.1 g, 0.45 mol) in tetrahydrofuran (1.5 L) at 0° C. was added lithium aluminium hydride (22.1 g, 0.58 mol) in several portions. The mixture was stirred at 0° C. for 2 h and quenched with 1 N sodium hydroxide solution. The mixture was filtered and the filter cake was washed with dichloromethane (4×300 mL). The combined organic layers were concentrated in vacuo. The crude product was purified by distillation under reduced pressure to afford 2-(tetrahydro-pyran-2-yl)-ethanol (53.5 g, 92% yield) as a colorless oil. quenched with 1 N sodium hydroxide solution The mixture was filtered the filter cake was washed with dichloromethane (4×300 mL) The combined organic layers were concentrated in vacuo The crude product was purified by distillation under reduced pressure

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

Procedure: 2-(Tetrahydro-2H-pyran-2-yl)ethanol (465 mg) was dissolved in dry DCM (10 mL) and triethylamine (996 mg) was added. The stirred solution was cooled in an ice bath under nitrogen and methanesulphonyl chloride (359 mg) was added dropwise over 5 mins. The reaction was allowed to warm to room temperature as the ice bath melted and was left for 16 h. The mixture was then shaken with saturated sodium bicarbonate solution and the aqueous layer was extracted with DCM (×2). The combined organic extracts were washed with brine, dried using a hydrophobic frit and evaporated to give the title compound as a brown oil (718 mg). The stirred solution was cooled in an ice bath under nitrogen the aqueous layer was extracted with DCM (×2) The combined organic extracts were washed with brine dried evaporated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of tetrahydro-2H-pyran-2-ylacetaldehyde (528 mg) in ethanol (5 mL) was added sodium borohydride granules (156 mg). The mixture was heated at 50° C. for 2 h under nitrogen. After cooling, the solvent was evaporated and the residue treated with brine. The mixture was acidified by careful addition of 2N HCl and this mixture was extracted with DCM (×3). The combined organics were washed with brine, dried using a hydrophobic frit and evaporated to give the title compound as a clear oil (465 mg). After cooling the solvent was evaporated the residue treated with brine The mixture was acidified by careful addition of 2N HCl this mixture was extracted with DCM (×3) The combined organics were washed with brine dried evaporated