185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Example 4; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; A three-neck-flask (0.25 L) is charged with quinidine (11 mmol), 3-isobutyl glutaric anhydride (10 mmol) and toluene (50 ml). The mixture is cooled at -55 C. Methanol (30 mmol) is added dropwise over a period of 10 min to the cooled suspension. The reaction is stirred at for 96 h. The solution is concentrated to dryness, and the resulting residue is dissolved in diethyl ether (65 ml). The solution is washed with HCl-2N, and the aqueous layer is back-extracted with ether. The combined organic layers are dried with MgSO4, and filtered. The filtrate is evaporated to dryness. Example 5; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a flame-dried 250 ml single, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30.5 vol) at -75 C. The reaction was stirred for 21 hours. The solution was concentrated to dryness, and the resulting residue was dissolved in diethyl ether (125 ml). The solution was washed with HCl-2N (40 ml¡Á3), and the aqueous layer was back-extracted with ether. The combined organic layers were evaporated until dryness, to give 3.56 g of a yellow oil of S-hemiester ((S)-3-((methoxycarbonyl)methyl)-5-methylhexanoic acid) (Optical purity 90%, Yield -91%). Example 6; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30.5 vol) at -50 C. The reaction was stirred for 2 hours. The slurry was washed with H2SO4-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to have 3.7 g yellow oil of S-Hemiester (Optical purity 90% Yield -95%). Example 7; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (12.5 g, 38.6 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30.5 vol) at -78 C. The reaction was stirred for 22.5 hours. The slurry was washed with HCl-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to have 3.63 g yellow oil of S-Hemiester (Optical purity 90%, Yield -93%). Example 8; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (33 ml, 10 vol) at -78 C. The reaction was stirred for 19 hours. The solution was washed with HCl-2N (25 ml¡Á3). The organic layer was evaporated until dryness, to give 3.38 g yellow oil of S-Hemiester (Optical purity 90%, Yield -87%). Example 9; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; Methanol (6.2 ml, 153 mmol) was added to a 250 ml three-necked, round-bottomed flask equipped with magnetic stirrer and charged with Quinidine (7.14 g, 22 mmol), 3-isobutyl glutaric anhydride (3.28 g, 19.3 mmol) and Toluene (100 ml, 30 vol) at -78 C. The reaction was stirred for 2 hours. The slurry was washed with H2SO4-2N (40 ml¡Á3). The organic layer was evaporated until dryness, to give 3.4 g yellow oil of S-Hemiester (Optical purity 95%, Yield -93%). Example 10; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (88 mmol) and Quinidine (100 mmol) in Toluene (30 vol) at -50 C., Methanol (273 mmol) was added drop-wise. The reaction was stirred at -50 C. for 17 h. The solution was washed with H2SO4-2N. The organic layer was evaporated to dryness to obtain S-Hemiester. (Optical purity -94%, Yield -94%). Example 11; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (19.3 mmol) and Quinidine (22 mmol) in Toluene (20 vol) at -50 C., Methanol (59.8 mmol) was added drop-wise. The reaction was stirred at -50 C. for 17 hours. The solution was washed with H2SO4-2N. The organic layer was evaporated to dryness to obtain S-Hemiester. (Optical purity -95%, Yield -89%). Example 12; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (19.3 mmol) and Quinidine (22 mmol) in Toluene (10 vol) at -50 C., Methanol (59.8 mmol) was added drop-wise. The reaction was stirred at -50 C. for 4 hours. The solution was washed with H2SO4-2N. The organic layer was evaporated to dryness to obtain S-Hemiester. (Optical purity -94%, Yield -92%). Example 13; Asymmetric Ring Opening of IBG-Anhydride with Chiral Alkaloide; To a stirred suspension of 3-isobutyl glutaric anhydride (19.3 m…
185815-59-2, The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Hedvati, Lilach; Gilboa, Eyal; Avhar-Maydan, Sharon; US2007/293694; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics