2-(prop-2-ynoxymethyl)furan

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

Procedure: To a suspension of sodium hydride (1.570 g, 39.2 mmol) in DMF (46 ml) stirred under argon at 0° C. a solution of 2-furanylmethanol (3.5 g, 35.7 mmol) in DMF (4 ml) was added dropwise over 20 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. 3-bromo-1-propyne (4.24 g, 35.7 mmol) 80% in toluene was dropped in 10 minutes at 0° C., then the mixture was left stirring at room temperature overnight. Water was added and then the mixture was extracted with ethyl ether 3 times. The organic phase was dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash chromatography on silica gel (Biotage SP1 instrument), eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15. Evaporation afforded the title compound (1.63 g, 35% yield). was added dropwise over 20 minutes the mixture was left stirring at room temperature overnight the mixture was extracted with ethyl ether 3 times The organic phase was dried over sodium sulphate concentrated under vacuum The residue was purified by flash chromatography on silica gel (Biotage SP1 instrument) eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15 Evaporation

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

Procedure: To a suspension of sodium hydride (1.570 g, 39.2 mmol) in DMF (46 ml) stirred under argon at 0° C. a solution of 2-furanylmethanol (3.5 g, 35.7 mmol) in DMF (4 ml) was added dropwise over 20 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. 3-bromo-1-propyne (4.24 g, 35.7 mmol) 80% in toluene was dropped in 10 minutes at 0° C., then the mixture was left stirring at room temperature overnight. Water was added and then the mixture was extracted with ethyl ether 3 times. The organic phase was dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash chromatography on silica gel (Biotage SP1 instrument), eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15. Evaporation afforded the title compound (1.63 g, 35% yield). was added dropwise over 20 minutes the mixture was left stirring at room temperature overnight the mixture was extracted with ethyl ether 3 times The organic phase was dried over sodium sulphate concentrated under vacuum The residue was purified by flash chromatography on silica gel (Biotage SP1 instrument) eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15 Evaporation

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

Procedure: To a suspension of sodium hydride (1.570 g, 39.2 mmol) in DMF (46 ml) stirred under argon at 0° C. was dropped a solution of 2-furanylmethanol (3.5 g, 35.7 mmol) in DMF (4 ml) in 20 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. 3-bromo-1-propyne (4.24 g, 35.7 mmol) 80% in toluene was dropped in 10 minutes at 0° C., then the mixture was left stirring at room temperature overnight. Water was added and then the mixture was extracted with ethyl ether 3 times. The organic phase was dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash chromatography on silica (Biotage SP1 instrument), eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15. Evaporation afforded the title compound (1.63 g). The reaction mixture was stirred at 0° C. for 15 minutes the mixture was left stirring at room temperature overnight the mixture was extracted with ethyl ether 3 times The organic phase was dried over sodium sulphate concentrated under vacuum The residue was purified by flash chromatography on silica (Biotage SP1 instrument) eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15 Evaporation

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

Procedure: To a mixture of sodium hydride (7.7 g, 190 mmol, 60% in oil) and tetrahydrofuran (100 mL) was added dropwise furfuryl alcohol (15 mL, 170 mmol) at 0° C. The reaction mixture was warmed to room temperature, N,N-dimethylformamide (30 mL) was added at that temperature, and the mixture was stirred at that temperature for 30 minutes. The reaction mixture was returned to 0° C., propargyl bromide (23 g, 190 mmol) was added at that temperature, and the mixture was stirred for 1 hour at room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with brine, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:30) to give the title compound (7.6 g, 32% yield). was returned to 0° C. the mixture was stirred for 1 hour at room temperature was then extracted with ethyl acetate The organic layer was washed with brine the solvent was distilled away under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:30)

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

Procedure: To a suspension of sodium hydride (1.570 g, 39.2 mmol) in DMF (46 ml) stirred under argon at 0° C. a solution of 2-furanylmethanol (3.5 g, 35.7 mmol) in DMF (4 ml) was added dropwise over 20 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. 3-bromo-1-propyne (4.24 g, 35.7 mmol) 80% in toluene was dropped in 10 minutes at 0° C., then the mixture was left stirring at room temperature overnight. Water was added and then the mixture was extracted with ethyl ether 3 times. The organic phase was dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash chromatography on silica gel (Biotage SP1 instrument), eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15. Evaporation afforded the title compound (1.63 g, 35% yield). was added dropwise over 20 minutes the mixture was left stirring at room temperature overnight the mixture was extracted with ethyl ether 3 times The organic phase was dried over sodium sulphate concentrated under vacuum The residue was purified by flash chromatography on silica gel (Biotage SP1 instrument) eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15 Evaporation

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

Procedure: To a suspension of sodium hydride (1.570 g, 39.2 mmol) in DMF (46 ml) stirred under argon at 0° C. was dropped a solution of 2-furanylmethanol (3.5 g, 35.7 mmol) in DMF (4 ml) in 20 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. 3-bromo-1-propyne (4.24 g, 35.7 mmol) 80% in toluene was dropped in 10 minutes at 0° C., then the mixture was left stirring at room temperature overnight. Water was added and then the mixture was extracted with ethyl ether 3 times. The organic phase was dried over sodium sulphate and concentrated under vacuum. The residue was purified by flash chromatography on silica (Biotage SP1 instrument), eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15. Evaporation afforded the title compound (1.63 g). The reaction mixture was stirred at 0° C. for 15 minutes the mixture was left stirring at room temperature overnight the mixture was extracted with ethyl ether 3 times The organic phase was dried over sodium sulphate concentrated under vacuum The residue was purified by flash chromatography on silica (Biotage SP1 instrument) eluting with a gradient cyclohexane/ethyl acetate 95/5 to 85/15 Evaporation