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Cacchi has established the superior reactivity of lithium salt (HCO2Li) in carboxylation reactions. Sodium formate (HCO2Na), however, was used as the formic salt throughout this study because of ease of availability."},{"key":"10.3987\/COM-08-S(F)16-45","unstructured":"12. A typical procedure for maleic anhydride formation: A mixture of HCO2Na (143 mg, 2.1 mmol), Ac2O (130 \u03bcL, 1.4 mmol), and i-Pr2NEt (245 \u03bcL, 1.4 mmol) was stirred at rt for 1 h. To this mixture were added triflate 7d (221 mg, 0.7 mmol) in DMF (1.0 mL + 0.5 mL x 2 used for rinsing), Pd(OAc)2 (7.9 mg, 0.035 mmol), and LiCl (89 mg, 2.1 mmol) sequentially, and the stirring was continued for another hour. The mixture was poured into a separatory funnel where it was partitioned between 2 N HCl and Et2O. Then, the organic extracts were combined, dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (Et2O\/hexane=1:3 v\/v) to give maleic anhydride 8d as a colorless oil. IR (neat) \u03bd 1771 cm-1; 1H NMR (400 MHz, CDCl3) \u03b4 2.68-2.63 (m, 4H), 1.86-1.79 (m, 4H), 1.60-1.55 (m, 4H); 13C NMR (100 MHz, CDCl3) \u03b4 165.9, 144.3, 25.8, 25.3, 22.9; MS m\/z: 180 (M+), 108 (100%); HRMS (EI) calcd for C10H12O3 (M+): 180.0786, found: 180.0789."},{"key":"10.3987\/COM-08-S(F)16-46","unstructured":"13. NMR data of mixed acetic anhydride 13: 1H NMR (300 MHz, CDCl3) \u03b4 3.56 (s, 3H), 2.63-2.58 (m, 1H), 2.49-2.38 (m, 3H), 2.09 (s, 3H), 1.90-1.59 (m, 6H); 13C NMR (75 MHz, CDCl3) \u03b4 169.0, 167.0, 157.0, 133.0, 116.4, 51.9, 29.9, 26.4, 26.3, 26.0, 24.6, 21.4."},{"key":"10.3987\/COM-08-S(F)16-47","doi-asserted-by":"publisher","DOI":"10.1021\/jo00129a023"},{"key":"10.3987\/COM-08-S(F)16-48","doi-asserted-by":"publisher","DOI":"10.1021\/ol990714i"},{"key":"10.3987\/COM-08-S(F)16-49","doi-asserted-by":"publisher","DOI":"10.1055\/s-1998-1885"},{"key":"10.3987\/COM-08-S(F)16-50","unstructured":"15. Synthesis of chaetomellic anhydride A (2): By applying the same protocol as that described above (note 12) to triflate 18 (1.59 g, 3.58 mmol), two materials consisting of desired anhydride 2 and its unstable precursor, a mixed acetic anhydride, were produced. Therefore, the mixture was diluted with CH2Cl2 followed by adding silica gel (ca. 20 g) to ensure complete cyclization of the precursor, yielding anhydride 2 as the sole product. Following filtration, concentration and purification by silica gel column chromatography (CH2Cl2) gave chaetomellic anhydride A (2) (935 mg, 87%) as a colorless oil, which solidified in a refrigerator (at ~3 \u00b0C) as a waxy solid. Chaetomellic anhydride A: IR (neat) \u03bd : 1771 cm-1; 1H NMR (400 MHz, CDCl3) \u03b4 2.45 (t, 2H, J=7 Hz), 2.07 (s, 3H), 1.63-1.54 (m, 2H), 1.34-1.25 (m, 22H), 0.88 (t, 3H, J=7 Hz); 13C NMR (100 MHz, CDCl3) \u03b4 166.1, 165.7, 144.6, 140.3, 31.9, 29.7-29.2 (9 peaks), 27.6, 24.5, 22.7, 14.1, 9.5; MS m\/z: 308 (M+), 126 (100%); HRMS (EI) calcd for C19H32O3 (M+) m\/z: 308.2351, found: 308.2355. The data are in full agreement with those reported.4a,f,m Mixed acetic anhydride: 1H NMR (300 MHz, CDCl3) \u03b4 3.57 (s, 3H), 2.25 (t, 2H, J=8 Hz), 2.09 (s, 3H), 1.88 (s, 3H), 1.37-1.16 (m, 24H), 0.88 (t, 3H, J=7 Hz)."}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:05:22Z","timestamp":1719259522000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-08-s%28f%2916"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009]]},"references-count":56,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2009]]}},"alternative-id":["COM-08-S(F)16"],"URL":"https:\/\/doi.org\/10.3987\/com-08-s(f)16","relation":{},"ISSN":["0385-5414"],"issn-type":[{"value":"0385-5414","type":"print"}],"subject":[],"published":{"date-parts":[[2009]]}}}