3,4-dihydro-2H-pyran-6-ylmethanol

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 5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran in 100 ml of dimethylformamide was added dropwise, whilst ice-cooling, to a mixture of 2.18 g of a 55% w/w suspension of sodium hydride in mineral oil and 100 ml of dimethylformamide. The mixture was stirred at room temperature for 60 minutes, after which 6.33 g of benzyl chloride were added. The reaction mixture was stirred for 16 hours, and then poured into 1 liter of water and extracted twice with ethyl acetate. The extract was washed with water, dried and condensed by evaporation under reduced pressure. The oily residue, 13 g, was subjected to column chromatography through 200 g of silica gel. The fraction eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume gave 9.40 g of the title compound as a colorless oily substance, boiling at 125°-130° C. (bath temperature)/1 mmHg (133 Pa). The reaction mixture was stirred for 16 hours extracted twice with ethyl acetate The extract was washed with water dried condensed by evaporation under reduced pressure The fraction eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume

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

Procedure: 5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran, 16.79 g of hexadecyl bromide and 8.22 g of pulverized 85% potassium hydroxide were mixed in 160 ml of toluene and heated under reflux for 2 hours. The mixtured was then cooled, washed with water, dried and condensed by evaporation under reduced pressure. The resulting oily residue, 17 g, was subjected to column chromatography through 400 g of silica gel. The fraction eluted with a 1:5 by volume mixture of diethyl ether and hexane gave 14.38 g of the title compound as a colorless oily substance. heated under reflux for 2 hours The mixtured was then cooled washed with water dried condensed by evaporation under reduced pressure The fraction eluted with a 1:5 by volume mixture of diethyl ether and hexane

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

Procedure: A solution of 5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran dissolved in 100 ml of dimethylformamide was added dropwise to a mixture of 2.18 g of sodium hydride (as a 55% w/w dispersion in mineral oil) and dimethylformamide, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour, after which 6.33 g of benzyl chloride were added to it. The mixture was stirred for 16 hours, after which it was poured into 1 liter of water. The resulting mixture was then extracted twice with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The oily residue (13 g) was subjected to column chromatography through 200 g of silica gel. 9.40 g of the title compound were obtained as a colorless oil from those fractions eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume. It boiled at 125°-130° C. (bath temperature)/1 mmHg (133 Pa). whilst ice-cooling The mixture was stirred for 16 hours The resulting mixture was then extracted twice with ethyl acetate The combined extracts were washed with water dried over anhydrous magnesium sulfate concentrated by evaporation under reduced pressure

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

Procedure: A solution of 5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran in 100 ml of dimethylformamide was added dropwise, whilst ice-cooling, to a mixture of 2.18 g of a 55% w/w suspension of sodium hydride in mineral oil and 100 ml of dimethylformamide. The mixture was stirred at room temperature for 60 minutes, after which 6.33 g of benzyl chloride were added. The reaction mixture was stirred for 16 hours, and then poured into 1 liter of water and extracted twice with ethyl acetate. The extract was washed with water, dried and condensed by evaporation under reduced pressure. The oily residue, 13 g, was subjected to column chromatography through 200 g of silica gel. The fraction eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume gave 9.40 g of the title compound as a colorless oily substance, boiling at 125°-130° C. (bath temperature)/1 mmHg (133 Pa). The reaction mixture was stirred for 16 hours extracted twice with ethyl acetate The extract was washed with water dried condensed by evaporation under reduced pressure The fraction eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume

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

Procedure: A solution of 5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran in 100 ml of dimethylformamide was added dropwise, whilst ice-cooling, to a mixture of 2.18 g of a 55% w/w suspension of sodium hydride in mineral oil and 100 ml of dimethylformamide. The mixture was stirred at room temperature for 60 minutes, after which 6.33 g of benzyl chloride were added. The reaction mixture was stirred for 16 hours, and then poured into 1 liter of water and extracted twice with ethyl acetate. The extract was washed with water, dried and condensed by evaporation under reduced pressure. The oily residue, 13 g, was subjected to column chromatography through 200 g of silica gel. The fraction eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume gave 9.40 g of the title compound as a colorless oily substance, boiling at 125°-130° C. (bath temperature)/1 mmHg (133 Pa). The reaction mixture was stirred for 16 hours extracted twice with ethyl acetate The extract was washed with water dried condensed by evaporation under reduced pressure The fraction eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume

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

Procedure: 5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran, 16.79 g of hexadecyl bromide and 8.22 g of pulverized 85% potassium hydroxide were mixed in 160 ml of toluene and heated under reflux for 2 hours. The mixtured was then cooled, washed with water, dried and condensed by evaporation under reduced pressure. The resulting oily residue, 17 g, was subjected to column chromatography through 400 g of silica gel. The fraction eluted with a 1:5 by volume mixture of diethyl ether and hexane gave 14.38 g of the title compound as a colorless oily substance. heated under reflux for 2 hours The mixtured was then cooled washed with water dried condensed by evaporation under reduced pressure The fraction eluted with a 1:5 by volume mixture of diethyl ether and hexane

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

Procedure: A solution of 5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran dissolved in 100 ml of dimethylformamide was added dropwise to a mixture of 2.18 g of sodium hydride (as a 55% w/w dispersion in mineral oil) and dimethylformamide, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour, after which 6.33 g of benzyl chloride were added to it. The mixture was stirred for 16 hours, after which it was poured into 1 liter of water. The resulting mixture was then extracted twice with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The oily residue (13 g) was subjected to column chromatography through 200 g of silica gel. 9.40 g of the title compound were obtained as a colorless oil from those fractions eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume. It boiled at 125°-130° C. (bath temperature)/1 mmHg (133 Pa). whilst ice-cooling The mixture was stirred for 16 hours The resulting mixture was then extracted twice with ethyl acetate The combined extracts were washed with water dried over anhydrous magnesium sulfate concentrated by evaporation under reduced pressure

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

Procedure: A solution of 5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran dissolved in 100 ml of dimethylformamide was added dropwise to a mixture of 2.18 g of sodium hydride (as a 55% w/w dispersion in mineral oil) and dimethylformamide, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour, after which 6.33 g of benzyl chloride were added to it. The mixture was stirred for 16 hours, after which it was poured into 1 liter of water. The resulting mixture was then extracted twice with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The oily residue (13 g) was subjected to column chromatography through 200 g of silica gel. 9.40 g of the title compound were obtained as a colorless oil from those fractions eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume. It boiled at 125°-130° C. (bath temperature)/1 mmHg (133 Pa). whilst ice-cooling The mixture was stirred for 16 hours The resulting mixture was then extracted twice with ethyl acetate The combined extracts were washed with water dried over anhydrous magnesium sulfate concentrated by evaporation under reduced pressure

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

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

Procedure: Methanesulfonyl chloride (17.9 mL, 232 mmol) was added dropwise to a solution of (5,6-dihydro-4H-pyran-2-yl)methanol (25.51 g, 193 mmol) [see Synlett, Vol. 5, p. 533 (1997)] and triethylamine (40.4 mL, 290 mmol) in dichloromethane (600 mL) under salt ice cooling over 15 minutes. After stirring at the same temperature for two hours, triethylamine (18.8 mL, 135 mmol) and methanesulfonyl chloride (7.5 mL, 97 mmol) were added, and the mixture was further stirred for 30 minutes. Water (300 mL) was added to the reaction solution, followed by extraction with ethyl acetate (1.5 L). The resulting organic layer was washed with water (300 mL) and brine (300 mL). The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under reduced pressure. The resulting crude title compound was used for the next reaction without purification. the mixture was further stirred for 30 minutes followed by extraction with ethyl acetate (1.5 L) The resulting organic layer was washed with water (300 mL) and brine (300 mL) The organic layer was dried over anhydrous sodium sulfate filtered the solvent was evaporated under reduced pressure The resulting crude title compound was used for the next reaction without purification

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

Procedure: 51.5 g (0.45 mol) of methanesulfonyl chloride are added dropwise to 45 g (0.39 mmol) of 6-hydroxymethyl-2,3-dihydropyran (Example 7a) and 50 g (0.5 mol) of triethylamine in 400 ml of methylene chloride at 0°-5° C. Stirring is carried out for 1 hour at 0° C. and the reaction mixture is poured onto water. The aqueous phase is separated off and the organic phase is extracted once again with water and is then dried over MgSO4 and evaporated down. 84 g of title compound are obtained as a red oil, which is used directly in the next reaction. the reaction mixture is poured onto water The aqueous phase is separated off the organic phase is extracted once again with water is then dried over MgSO4 evaporated down