2-tert-butylpropane-1,3-diol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-t-butylpropane-1,3-diol (11.0 g.) (E.L. Eliel et al J. Amer Chem Soc. 1968, 90, 3444) was stirred in dry toluene (200 ml), at 20° C. Sodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane, was added carefully to the stirred mixture. The mixture was stirred at 120° C. for 30 minutes and cooled. Benzyl bromide (9.5 ml) was added dropwise and the mixture heated at 130°, with stirring for 6 hours. The mixture was cooled, water was added and the mixture extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with 1:4 diethyl ether: hexane. 2-Benzyloxymethyl-3,3-dimethyl-butan-1-ol (8.0 g) was obtained as a colourless Sodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane was added carefully to the stirred mixture cooled Benzyl bromide (9.5 ml) was added dropwise the mixture heated at 130° with stirring for 6 hours The mixture was cooled water was added the mixture extracted with diethyl ether The ethereal extracts were washed with water dried over anhydrous magnesium sulphate evaporated in vacuo The residue was purified by chromatography on silica eluting with 1:4 diethyl ether

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-t-butylpropane-1,3-diol (11.0 g.) (E.L. Eliel et al J. Amer Chem Soc. 1968, 90, 3444) was stirred in dry toluene (200 ml), at 20° C. Sodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane, was added carefully to the stirred mixture. The mixture was stirred at 120° C. for 30 minutes and cooled. Benzyl bromide (9.5 ml) was added dropwise and the mixture heated at 130°, with stirring for 6 hours. The mixture was cooled, water was added and the mixture extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with 1:4 diethyl ether: hexane. 2-Benzyloxymethyl-3,3-dimethyl-butan-1-ol (8.0 g) was obtained as a colourless Sodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane was added carefully to the stirred mixture cooled Benzyl bromide (9.5 ml) was added dropwise the mixture heated at 130° with stirring for 6 hours The mixture was cooled water was added the mixture extracted with diethyl ether The ethereal extracts were washed with water dried over anhydrous magnesium sulphate evaporated in vacuo The residue was purified by chromatography on silica eluting with 1:4 diethyl ether

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-t-butylpropane-1,3-diol (11.0 g.) (E.L. Eliel et al J. Amer Chem Soc. 1968, 90, 3444) was stirred in dry toluene (200 ml), at 20° C. Sodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane, was added carefully to the stirred mixture. The mixture was stirred at 120° C. for 30 minutes and cooled. Benzyl bromide (9.5 ml) was added dropwise and the mixture heated at 130°, with stirring for 6 hours. The mixture was cooled, water was added and the mixture extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with 1:4 diethyl ether: hexane. 2-Benzyloxymethyl-3,3-dimethyl-butan-1-ol (8.0 g) was obtained as a colourless Sodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane was added carefully to the stirred mixture cooled Benzyl bromide (9.5 ml) was added dropwise the mixture heated at 130° with stirring for 6 hours The mixture was cooled water was added the mixture extracted with diethyl ether The ethereal extracts were washed with water dried over anhydrous magnesium sulphate evaporated in vacuo The residue was purified by chromatography on silica eluting with 1:4 diethyl ether

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Add 2.7 ml of 11.25 N sodium hydroxide solution to a solution of 1974 mg (14.93 mmol) 2-tert.-butylpropane-1,3-diol in 25 ml toluene, 8 ml 1,2-dimethoxyethane and 8 ml water at 70° C. After adding 101 mg (0.30 mmol) tetra-n-butylammonium hydrogensulphate and 1000 mg (2.99 mmol) 4-chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine, stir the reaction mixture for 17 h at 70° C. After cooling to room temperature, adjust to pH 7 with concentrated hydrochloric acid. Extract with dichloromethane. Wash the organic phase with satd. sodium chloride solution, dry over sodium sulphate, and filter. Concentrate the filtrate by vacuum evaporation. Mix the residue with methanol, filter, and wash with diethyl ether. Purify the filtrate by preparative RP-HPLC (gradient: water/acetonitrile). 275 mg (21% of theor.) of the desired product (racemate) is obtained. After cooling to room temperature Extract with dichloromethane Wash the organic phase with satd sodium chloride solution, dry over sodium sulphate filter Concentrate the filtrate by vacuum evaporation Mix the residue with methanol filter wash with diethyl ether Purify the filtrate by preparative RP-HPLC (gradient: water/acetonitrile)

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-t-butylpropane-1,3-diol (11.0 g.) (E.L. Eliel et al J. Amer Chem Soc. 1968, 90, 3444) was stirred in dry toluene (200 ml), at 20° C. Sodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane, was added carefully to the stirred mixture. The mixture was stirred at 120° C. for 30 minutes and cooled. Benzyl bromide (9.5 ml) was added dropwise and the mixture heated at 130°, with stirring for 6 hours. The mixture was cooled, water was added and the mixture extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by chromatography on silica, eluting with 1:4 diethyl ether: hexane. 2-Benzyloxymethyl-3,3-dimethyl-butan-1-ol (8.0 g) was obtained as a colourless Sodium hydride (2.4 g., 80% dispersion in oil), previously washed with hexane was added carefully to the stirred mixture cooled Benzyl bromide (9.5 ml) was added dropwise the mixture heated at 130° with stirring for 6 hours The mixture was cooled water was added the mixture extracted with diethyl ether The ethereal extracts were washed with water dried over anhydrous magnesium sulphate evaporated in vacuo The residue was purified by chromatography on silica eluting with 1:4 diethyl ether