dimethyl pentanedioate

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

Procedure: 196 parts by wt. of furfuryl alcohol and 160 parts by wt. dimethyl glutarate (stoichiometric proportions) were mixed and 0.5-0.75% wt. sodium metal added. The mixture was heated to a temperature in the range from 214°-240° F. under a nitrogen atmoshpere. Methanol was evolved and removed as the reaction progressed. After a period of 4 hours, a waxy solid was obtained. After washing the product with water, the residure was a liquid which was identified as difurfuryl glutarate by gas chromatography and mass spectrometric analysis. The mixture was heated to a temperature in the range from 214°-240° F. under a nitrogen atmoshpere removed as the reaction a waxy solid was obtained After washing the product with water

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.0 g of dimethyl glutarate were added to 8.70 g of N-methyl-tryptamine (i.e., 3-(2-methylaminoethyl)-indole), and the mixture was heated at 150° C. under reduced pressure for 2 hours. After the reaction was completed, the mixture was acidified with dilute hydrochloric acid and then extracted with ethyl acetate. The extract was washed with water, an aqueous saturated sodium bicarbonate solution and an aqueous saturated sodium chloride solution, successively. The washed extract was dried and evaporated under reduced pressure to remove solvent. The residue thus obtained was recrystallized from a mixture of ethyl acetate and n-hexane. 11.3 g of N-methyl-N-(4-methoxycarbonylbutyryl)-tryptamine (i.e., 3-[2-(N-methyl-4-methoxycarbonylbutanamido)ethyl]-indole) were thereby obtained. M.p. 101°-102° C. Yield: 70% extracted with ethyl acetate The extract was washed with water The washed extract was dried evaporated under reduced pressure to remove solvent The residue thus obtained was recrystallized from a mixture of ethyl acetate and n-hexane

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

Procedure: To a suspension of potassium tert-butoxide (7.29 g, 64.9 mmol) in t-butylmethyl ether (100 mL) was added a solution of dimethyl pentanedioate (5.2 g, 32.5 mmol) and methyl formate (1.950 g, 32.5 mmol) in t-butylmethyl ether (50 mL). The mixture was stirred overnight and concentrated to dryness afford the yellow oil. The oil was dissolved in methanol (80 mL), to which thiourea (2.72 g, 35.7 mmol) was added. The mixture was heated to reflux overnight. The result mixture was concentrated and dissolved in water, adjust pH to 3 with AcOH. The solution was extracted with DCM three times. The combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound (2.1 g, 9.80 mmol, 30.2% yield). concentrated to dryness afford the yellow oil was added The mixture was heated to reflux overnight The result mixture was concentrated dissolved in water The solution was extracted with DCM three times The combined organic layers were dried over Na2SO4 filtered concentrated

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

Procedure: To a suspension of potassium tert-butoxide (7.29 g, 64.9 mmol) in t-butylmethyl ether (100 mL) was added a solution of dimethyl pentanedioate (5.2 g, 32.5 mmol) and methyl formate (1.950 g, 32.5 mmol) in t-butylmethyl ether (50 mL). The mixture was stirred overnight and concentrated to dryness afford the yellow oil. The oil was dissolved in methanol (80 mL), to which thiourea (2.72 g, 35.7 mmol) was added. The mixture was heated to reflux overnight. The result mixture was concentrated and dissolved in water, adjust pH to 3 with AcOH. The solution was extracted with DCM three times. The combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound (2.1 g, 9.80 mmol, 30.2% yield). concentrated to dryness afford the yellow oil was added The mixture was heated to reflux overnight The result mixture was concentrated dissolved in water The solution was extracted with DCM three times The combined organic layers were dried over Na2SO4 filtered concentrated

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

Procedure: To a suspension of potassium tert-butoxide (7.29 g, 64.9 mmol) in t-butylmethyl ether (100 mL) was added a solution of dimethyl pentanedioate (5.2 g, 32.5 mmol) and methyl formate (1.950 g, 32.5 mmol) in t-butylmethyl ether (50 mL). The mixture was stirred overnight and concentrated to dryness afford the yellow oil. The oil was dissolved in methanol (80 mL), to which thiourea (2.72 g, 35.7 mmol) was added. The mixture was heated to reflux overnight. The result mixture was concentrated and dissolved in water, adjust pH to 3 with AcOH. The solution was extracted with DCM three times. The combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound (2.1 g, 9.80 mmol, 30.2% yield). concentrated to dryness afford the yellow oil was added The mixture was heated to reflux overnight The result mixture was concentrated dissolved in water The solution was extracted with DCM three times The combined organic layers were dried over Na2SO4 filtered concentrated

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

Procedure: 196 parts by wt. of furfuryl alcohol and 160 parts by wt. dimethyl glutarate (stoichiometric proportions) were mixed and 0.5-0.75% wt. sodium metal added. The mixture was heated to a temperature in the range from 214°-240° F. under a nitrogen atmoshpere. Methanol was evolved and removed as the reaction progressed. After a period of 4 hours, a waxy solid was obtained. After washing the product with water, the residure was a liquid which was identified as difurfuryl glutarate by gas chromatography and mass spectrometric analysis. The mixture was heated to a temperature in the range from 214°-240° F. under a nitrogen atmoshpere removed as the reaction a waxy solid was obtained After washing the product with water

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

Procedure: 196 parts by wt. of furfuryl alcohol and 160 parts by wt. dimethyl glutarate (stoichiometric proportions) were mixed and 0.5-0.75% wt. sodium metal added. The mixture was heated to a temperature in the range from 214°-240° F. under a nitrogen atmoshpere. Methanol was evolved and removed as the reaction progressed. After a period of 4 hours, a waxy solid was obtained. After washing the product with water, the residure was a liquid which was identified as difurfuryl glutarate by gas chromatography and mass spectrometric analysis. The mixture was heated to a temperature in the range from 214°-240° F. under a nitrogen atmoshpere removed as the reaction a waxy solid was obtained After washing the product with water

Conditions: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cold (−78° C.) solution of N,N,N′,N′-tetramethylethylenediamine (TMEDA) (4.06 mL, 26.9 mmol) in dry THF (50 mL) under an atmosphere of Ar was added n-BuLi (2.5 M in hexanes, 10.7 mL, 26.9 mmol). 2-Bromo-3-methylpyridine (3.0 mL, 26.9 mmol) was added dropwise and the temperature was raised to −55° C. for 30 minutes. The reaction mixture turned red. It was then cooled to −78° C. and dimethyl glutarate (1.65 mL, 11.2 mmol) was added. The reaction mixture was stirred at −78° C. for 1 h. Water (200 mL) was added and the mixture was extracted with CH2Cl2 (3 times 200 mL). The combined organic extracts were washed with brine (200 mL), were dried over mgSO4, filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (1:1 EtOAc:hexanes) to provide 1.5 g (48%) of 1,5-bis-(3-methyl-pyridin-2-yl)-pentane-1,5-dione as a white solid. 1H NMR(CDCl3) δ 2.00 (p, 2H, J=7.5 Hz), 2.44 (s, 6H), 3.19 (t, 4H, J=7.5 Hz), 7.18 (dd, 2H, J=7.8, 4.2 Hz), 7.43 (d, 2H, J=7.8 Hz), 8.33 (d, 2H, J=4.2 Hz). It was then cooled to −78° C. the mixture was extracted with CH2Cl2 (3 times 200 mL) The combined organic extracts were washed with brine (200 mL) were dried over mgSO4 filtered concentrated The crude material was purified by flash column chromatography on silica gel (1:1 EtOAc:hexanes)

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

Procedure: 196 parts by wt. of furfuryl alcohol and 160 parts by wt. dimethyl glutarate (stoichiometric proportions) were mixed and 0.5-0.75% wt. sodium metal added. The mixture was heated to a temperature in the range from 214°-240° F. under a nitrogen atmoshpere. Methanol was evolved and removed as the reaction progressed. After a period of 4 hours, a waxy solid was obtained. After washing the product with water, the residure was a liquid which was identified as difurfuryl glutarate by gas chromatography and mass spectrometric analysis. The mixture was heated to a temperature in the range from 214°-240° F. under a nitrogen atmoshpere removed as the reaction a waxy solid was obtained After washing the product with water

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

Procedure: 8.17 g (0.19 mole) of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 25 g (0.16 mole) of dimethyl glutarate and 23.4 g (0.16 mole) of 1-naphthaldehyde dissolved in 200 ml of anhydrous methanol. The mixture was heated under reflux for 30 minutes, after which 190 ml (0.19 mole) of a 1N aqueous solution of sodium hydroxide were added to it, and the mixture was again heated under reflux for 1 hour. The solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with water and washed with diethyl ether. The aqueous layer was acidified and then extracted with diethyl ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then diisopropyl ether was added to the residue to precipitate crystals, which were collected by filtration to give 18.5 g of 2-(1 -naphthylmethylene)glutaric acid. The mixture was heated under reflux for 30 minutes the mixture was again heated under reflux for 1 hour The solvent was removed by distillation under reduced pressure the resulting residue was mixed with water washed with diethyl ether extracted with diethyl ether The ethereal layer was washed with a saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure diisopropyl ether was added to the residue to precipitate crystals, which were collected by filtration

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

Procedure: 8.17 g (0.19 mole) of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, with ice-cooling, to a solution of 25 g (0.16 mole) of dimethyl glutarate and 23.4 g (0.16 mole) of 1-naphthaldehyde dissolved in 200 ml of anhydrous methanol. The mixture was heated under reflux for 30 minutes, after which 190 ml (0.19 mole) of a 1N aqueous solution of sodium hydroxide were added and the mixture was heated under reflux for a further 1 hour. The solvent was then removed by distillation under reduced pressure, and the residue was mixed with water and then washed with diethyl ether. The aqueous layer was acidified and extracted with diethyl ether. The ethereal layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then diisopropyl ether was added to the residue to precipitate crystals, which were collected by filtration to give 18.5 g of 2-(1 -naphthylmethylene)glutaric acid. The mixture was heated under reflux for 30 minutes the mixture was heated under reflux for a further 1 hour The solvent was then removed by distillation under reduced pressure the residue was mixed with water washed with diethyl ether extracted with diethyl ether The ethereal layer was washed with a saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure diisopropyl ether was added to the residue to precipitate crystals, which were collected by filtration

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

Procedure: Furfuryl alcohol (196 parts, 2 moles ) and 160 parts (1 mole) of dimethyl glutarate were mixed, and 0.5-0.75 percent of sodium metal was added. The mixture was heated to a temperature in the range from 101°-115° C. under a nitrogen atmosphere. Methanol was evolved and removed as the reaction progressed. After a period of four hours, a waxy solid was obtained. After washing the product with water, the residue was a liquid which was identified as difurfuryl glutarate by gas chromatography and mass spectrometric analysis. The mixture was heated to a temperature in the range from 101°-115° C. under a nitrogen atmosphere removed as the reaction a waxy solid was obtained After washing the product with water