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With sodium hydroxide; In methanol; |
REFERENTIAL EXAMPLE 161 1-(Methoxycarbonyl)cyclopropanecarboxylic acid: Dimethyl 1,1-cyclopropanecarboxylate (25 g) was dissloved in methanol (250 ml), and the solution was cooled with ice. A 1N aqueous solution of sodium hydroxide (158 ml) was then added dropwise, and the resultant mixture was warmed to room temperature and stirred overnight. After methanol was distilled off, the residue was washed with chloroform, and a water layer was cooled with ice, adjusted to pH 2 with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (16.8 g). 1H-NMR (CDCl3) delta: 1.76-1.80(2H,m), 1.82-1.88(2H,m), 3.79(3H,s), 12.73(1H,br). |
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Method C; <strong>[6914-71-2]Dimethyl 1,1-cyclopropanedicarboxylate</strong> (5 ml) was mixed with NaOH (1.4 g) in MeOH (40 ml)/water (4 ml). The reaction mixture was stirred at RT overnight and the solvent was evaporated. To the residue was added ether (50 ml), water (50 ml) and extracted once. The aqueous layer was acidified with 6N HCl and extracted three times with ether, the combined organic layer was washed with brine, dried and evaporated to give 1-(methoxycarbonyl)cyclopropanecarboxylic acid (4 g). |
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With sodium hydroxide; In methanol; water; at 0 - 20℃; |
[Referential Example 161] 1-(Methoxycarbonyl)cyclopropanecarboxylic acid: dimethyl 1,1-cyclopropanecarboxylate (25 g) was dissloved in methanol (250 ml), and the solution was cooled with ice.. A 1N aqueous solution of sodium hydroxide (158 ml) was then added dropwise, and the resultant mixture was warmed to room temperature and stirred overnight.. After methanol was distilled off, the residue was washed with chloroform, and a water layer was cooled with ice, adjusted to PH 2 with concentrated hydrochloric acid and extracted with ethyl acetate.. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (16.8 g).1H-NMR (CDCl3) delta: 1.76-1.80(2H,m), 1.82-1.88(2H,m), 3.79(3H,s), 12.73(1H,br). |
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<strong>[6914-71-2]Dimethyl 1,1-cyclopropanedicarboxylate</strong> (5 ml) was mixed with NaOH (1.4 g) in MeOH (40 ml)/water (4 ml). The reaction mixture was stirred at RT overnight and the solvent was evaporated. To the residue was added ether (50 ml), water (50 ml) and extracted once. The aqueous layer was acidified with 6N HCl and extracted three times with ether, the combined organic layer was washed with brine, dried and evaporated to give 1-(methoxycarbonyl)cyclopropanecarboxylic acid (4 g). |
| 1.58 g |
With water; sodium hydroxide; In methanol; at 20℃; for 23h; |
(1) To a solution of dimethyl 1,1-cyclohexanedicarboxylate (2.08 g) in methanol (15 mL) was added a 1Naqueous sodium hydroxide solution (13.2 mL), and the mixture was stirred at room temperature for 23 hours. Themethanol was distilled off under reduced pressure, and the residue was washed with n-hexane. To an aqueous layerwas added 1N hydrochloric acid (10 mL), and the mixture was extracted with chloroform. The extract was washed withsaturated brine, and dried over anhydrous magnesium sulfate. After drying, concentration under reduced pressureprovided Compound 2 (1.58 g) as a colorless oil. |
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With water; lithium hydroxide; In methanol; at 20℃; for 1h; |
Dimethyl cyclopropane dicarboxylate (10.12 g, 63.99 mmol) was dissolved in 100 mL (1:1 V:V) CH3OH/H2O and stirred at room temperature. Lithium hydroxide (2.68 g, 63.99 mmol) dissolved in 20 ml H2O was slowly added to the above solution for three times at room temperature, and then the mixture was allowed to react for 1 h with stirring. After the reaction was completed, the resultant was adjusted to pH3 with dilute hydrochloric acid, extracted with DCM, and dried over anhydrous sodium sulfate. The product without purification was to be used in the next step. |
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With water; lithium hydroxide; In methanol; at 20℃; for 1h; |
A solution of dimethyl cyclopropane-1,1-dicarboxylate (10.12 g,63.99 mmol) in MeOH/H2O (100 mL, 1:1 V:V), stirring in room temperature,was treated dropwise with a solution of lithium hydroxide(2.68 g, 63.99 mmol) in 20 mL H2O. Stir for one hour after dropwise.Then adjust pH to 3 with dilute hydrochloric acid, extract with dichloromethane(50 mL) for three times, without purification go on nextstep. |
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