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With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 16.0h;Inert atmosphere;
To a suspension of LiAlH4 (0.835 g, 22.00 mmol, 2.20 equiv) in THF (50 mL) was slowly added a solution of undecane-1,11-dioic acid (10; 2.443 g, 10.00 mmol, 1.00 equiv) in THF (100 mL) at 0 C. This mixture was stirred at r.t. for 16 h. The reaction was stopped by addition of a 30 wt% aqueous solution of citric acid at 0 C (100 mL). The mixture was extracted with Et2O (3 80 mL) and the combined organic phases were washed with H2O, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The residue was dissolved in Et2O and washed again with H2O. The organic phase was dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The product was used without further purification. Yield: 1.905 g (8.804 mmol, 88%); colourless solid; mp 74-75 C (lit.6b mp 75-76 C); Rf = 0.39 (cyclohexane/EtOAc, 2:3). IR (ATR): 3236, 2917, 2849, 1486, 1472, 1462, 1405, 1357, 1344, 1324, 1302, 1257, 1210, 1187, 1123, 1057, 1037, 1019, 1002, 973, 958, 920, 876, 831, 764, 731, 720, 687 cm-1. 1H NMR (CDCl3, 500 MHz): delta = 3.65 (t, J = 6.6 Hz, 4 H, 1-H, 13-H), 1.57 (quin, J = 6.6 Hz, 4 H, 2-H, 12-H), 1.38-1.25 (m, 20 H, 3-H to 11-H, OH). 13C NMR (CDCl3, 125 MHz): delta = 63.3, 33.0, 29.74, 29.73, 29.70, 29.6, 25.9.
General procedure: Under an atmosphere of N2, a suspension of LiAlH4 (228 mg, 6.01 mmol, 11.6 equiv) in dry THF (6 mL) was stirred at rt for 5 min. The mixture was cooled to 0 C, and a solution of pentadecanolide (500 mg, 2.08 mmol, 1 equiv) in THF (6 mL) was added. The reaction mixture was brought to rt and then stirred at reflux temperature for 2 h. The mixture was cooled to 0 C and then an aqueous solution of NaOH (2 M, 2 mL) was added. A white precipitate was formed and the mixture was stirred at reflux temperature for 0.5 h. The mixture was extracted with Et2O (2 × 50 mL). The combined organic extracts were washed with brine (2 × 20 mL), dried (Na2SO4), and concentrated. High-vacuum drying gave 1,15-pentadecanediol (482 mg, 1.97 mmol, 95%) as a white solid;
General procedure: Samples of 1,10-decanediol, DEDOL (98% pure) and 1,12-dodecanediol, DODOL (99% pure) fromSigma-Aldrich were used as received. Then, 1,11-undecanediol (UNDOL) and 1,13-tridecanediol(TRDOL) were synthesized from the corresponding dicarboxylic acids by a reduction procedurereported elsewhere [41]. First, N-methylmorpholine (1.01 mL, 9.24 mmol) and ethyl chloroformate(0.88 mL, 9.24 mmol) [42] were mixed with a dissolution (2 C) prepared with 1 g of undecanedioicacid (4.62 mmol) in 50 mL of THF. This mixture was stirred for 15 min and a precipitate ofN-methylmorpholine hydrochloride was obtained. This precipitate is filtered, washed with THFand mixed at 2 C with 7 mL of an aqueous sodium borohydride solution (0.56 g, 14.78 mmol). Then,120 mL of water was added after degassing the solution. Finally, ethyl acetate was used to obtainthe organic extract that, subsequently, was dried over sodium sulfate. Purified UNDOL is obtainedfor concentrating them under reduced pressure and recrystallized in ethyl ether. All this synthesiswas also used to obtain TRDOL but, in this case, 1,13-tridecanedioic acid was selected as the startingproduct. TRDOL was recrystallized in toluene instead of ethyl ether in order to evaluate possiblechanges on crystallite morphology of isostructural compounds.
With lithium aluminium tetrahydride; In tetrahydrofuran; for 12.0h;Inert atmosphere;
To a solution ofbrassylic acid (2, 1.2210 g, 5mmol) in anhydrous THF(15 mL), LiAlH4 (0.5690 g, 15mmol) was added in dry threeneckedround-bottomed flask equipped in batches undernitrogen atmosphere at 0C. The mixture was stirred at roomtemperature for 12 h. After completion, the reaction wasquenched by 10% HCl aqueous solution in ice bath until gasproduction ceased.The organic layer was separated, filtered,and concentrated under reduced pressure. The residue waswashed with ethyl acetate and dried over anhydrous MgSO4.The extract was evaporated and dried to give crude 1,13-tridecanediol (3, 1.0818g) as white solid. 1H-NMR (CDCl3,500MHz) 3.61 (dd, , J = 11.0, 6.2Hz, 4H), 2.35 (s, 1H),2.26 (s, 1H), 1.62-1.50 (m, 4H), 1.39-1.20 (m, 18H); 13C-NMR(CDCl3, 125MHz) 77.2, 77.0, 76.7, 32.6(2), 29.5(3), 29.4(2),29.3(2), 25.6; HRMS (ESI-TOF) m/z: Calcd. for C13H29O2+217.2183 ([M + H]+). Found: 217.2205.
Acetic acid (R)-4-[13-((R)-1-acetoxymethyl-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-4-yloxy)-tridecyloxy]-1-hydroxymethyl-3-oxo-1,3-dihydro-isobenzofuran-1-ylmethyl ester[ No CAS ]